Иминиевые илиды из монофторкарбена — новые синтетические блоки для получения азот-и фторсодержащих органических соединений
Диссертация
Научная новизна. Разработан новый метод генерирования фторкарбена, заключающийся в восстановлении дибромфторметана активным свинцом в присутствии источника бромид-ионов. Изучена реакционная способность неизвестных ранее монофторзамещенных азометин-илидов. Показано, что они способны вступать в реакции 1,3-диполярного циклоприсоединения к электрон-дефицитной кратной связи углерод-углерод, а также… Читать ещё >
Список литературы
- Begue J. P.- Bonnet-Delpon D. Chimie bioorganique et medicinale du fluor, EDP Sciences/CNRS, 2005.
- Shah P.- Westwell A. D. The role of fluorine in medicinal chemistry. Il J. Enz. Inhib. Med. Chem. 2007, 22, 527−540.
- Ismail F. M. D. Important fluorinated drugs in experimental and clinical use. // J. Fluor. Chem. 2002,118, 27−33.
- Isanbor Ch.- O’Hagan D. Fluorine in medicinal chemistry: a review of anti-cancer agents. // J. Fluor. Chem. 2006,127, 303−319.
- Dolbier Jr. W. R. Fluorine chemistry at the millennium. II J. Fluor. Chem. 2005,126,157−163.
- Smart В. E. Fluorine substituent effects (on bioactivity). // J. Fluor. Chem. 2001,109, 3.
- Leroux F.- Jeschke P.- Schlosser M. a-Fluorinated ethers, thioethers and amines: anomerically biased species. // Chem. Rev. 2005,105, 827.
- Cartwright D. Recent Developments in Fluorine-Containing Agrochemicals, in: Organofluorine Chemistry: Principles and Commercial Applications. Banks R. E., Smart В. E., Tatlow J. C., Eds- Plenum, New York, 1994, p. 237−262.
- Prakesch M.- Gree D.- Chandrasekhar S.- Gree R. Synthesis of fluoro analogues of unsaturated fatty acids and corresponding acyclic metabolites. // Eur. J. Org. Chem., 2005, 1221−1232 (см. также цит. ссылки).
- Liu X.- Deng G.- Chu X.- Li N.- Wu L.- Li D. Formation of an enolate intermediate is required for the reaction catalyzed by 3-hydroxyacyl-CoA dehydrogenase. // Bioorg. Med. Chem. Lett. 2007, 77,3187−3190.
- Purser S.- Moore P. R.- Swallow S.- Gouverneur V. Fluorine in medicinal chemistry. // Chem. Soc. Rev. 2008, 37, 320−330.
- Liu J.- Ni С.- Li Y.- Zhang L.- Wang G.- Hu J. Facile preparation of difluoromethyl- and monofluoromethyl-containing amides via Ritter reaction. // Tetrahedron Lett. 2006, 47, 6753−6756.
- Tayer A. M. Fabulous fluorine. // Chem. Eng. News 2006, 84, 15−24.
- Allmendinger T.- Furet P.- Hungerbuhler E. Fluoroolefin dipeptide isosters -1. Tetrahedron Lett. 1990, 31, 7297−7300.j
- Mikami K.- Itoh Y.- Yamanaka M. Fluorinated carbonyl and olefinic compounds: basic character and asymmetric catalytic reactions. // Chem. Rev. 2004,104, 1−16.
- Berkowitz D. В.- Bose M. (a-Monofluoroalkyl)phosphonates: a class of isoacidic and «tunable» mimics of biological phosphates. II J. Fluor. Chem. 2001,112, 13−33.
- O’Hagan D.- Rzepa H.S. Some influences of fluorine in bioorganic chemistry. // Chem. Commun. 1997, 645−652.
- Rozen S. Attaching the fluorine atom to organic molecules using BrF3 and other reagents directly derived from F2. II Acc. Chem. Res. 2005, 38, 803.
- Hutchinson J.- Sandford G. Elemental fluorine in organic chemistry. // Top. Curr. Chem. 1997, 193, 1−43.
- Ma J.-A.- Cahard D. Asymmetric fluorination, trifluoromethylation and perfluoroalkylation reactions. 11 Chem. Rev. 2004,104, 6119−6146.
- Percy J. M. Building block approaches to aliphatic organofluorine compounds. // Top. Curr. Chem. 1997, 193, 131−195.
- Bhadury P. S.- Palit M.- Sharma M.- Raza S. K.- Jaiswal D. K. Fluorinated phosphonium ylides: versatile in situ Wittig intermediates in the synthesis of hydrofluorocarbons. // J. Fluor. Chem. 2002, 116, 75−80.
- Kawabata N.- Tanimoto M.- Fujiwara S. Synthesis of monohalocyclopropane derivatives from olefins by the reaction with halomethanes and copper. // Tetrahedron 1979, 35, 1919−1923.
- Weyerstahl P.- Mathias R.- Blume G. Darstellung von 1 -Fluor- 1-jod-cyclopropanen. Tetrahedron Lett. 1973, 611−612.
- Nishimura B. J.- Furukawa J. The formation of a halogenocarbenoid of zinc. A novel synthetic route to halogenocyclopropane derivatives. // Chem. Commun. 1971, 1375−1376.
- Hahnfeld J. L.- Burton D. J. Monofluorocarbene: the synthesis of fluorocyclopropanes. // Tetrahedron Lett. 1975, 1819−1822.
- Schlosser M.- Heinz G. Monofluorocarbene and its syn/anti selectivity. //Angew. Chem. Int. Ed.: 1968, 7, 820−821.
- Fouque E.- Rousseau G.- Seyden-Penne J. Iterative synthesis of selectively substituted a, P-unsaturated and saturated medium-ring lactones. // J. Org. Chem. 1990, 55,4807−4817.
- Burton, D. J.- Hahnfeld, J. L. in: Fluorine Chemistry Reviews, Tarrant, P., Ed., 8, 119−188. Marcel Dekker, New York, 1977.
- Seyferth D.- Darra К. V. Halomethylmetal compounds. XXXI. Phenyl (fluorodichIoromethyl)mercury, a useful source of fluorocarbene. // J. Org. Chem. 1970,35, 1297−1302.
- Weyerstahl P.- Blume G.- Muller С. Zur Darstellung von 1 -Fluor- 1-brom und1.-Fluor-1-chlor-cyclopropanen. // Tetrahedron Lett. 1971, 3869−3872.
- Schlosser M.- Van Chau L. 283. Fluoroorganische Synthesen V. Darstellung und Abwandlung von Chlorofluorocyclopropanen ein gezielter Zugang zu Fluoroallylalkoholen. И Helv. Chim. Acta 1975, 58, 2595−2604.
- Волчков H. В.- Заболотских А. В.- Игнатенко А. В.- Нефедов О. М. Взаимодействие фторхлоркарбена с циклопентадиеном, инденом и их алкилпроизводными в условиях межфазного катализа. II Изв. Акад. Наук СССР, сер. хим. 1990, 39, 1609−1613.
- Burton D. J.- Hahnfeld J. L. Fluorochloro-, fluorobromo-, and monofluorocarbene generation via organolithium reagents. II J. Org. Chem. 1977, 42, 828−831.
- Wijsman G. W.- Boesveld W. M.- Beekman M. C.- Goedheijt M. S.- van Baar B. L. M.- de Kanter F. J. J.- de Wolf W. H.- Bickelhaupt F. Unusual reactions of halo5]metacyclophanes.
- Eur. J. Org. Chem. 2002, 614−629.
- Muller С.- Stier F.- Weyerstahl P. Darstellung, Ringoffnungsreaktionen und Halogen/Lithium Austausch von 1-Brom-l-fluorocyclopropanen. II Chem. Ber. 1977,110, 124−137.
- Mathias R.- Weyerstahl P. Darstellung und Eigenschaften von 1,1-Diiod- und 1 -Iod-1 -x-cyclopropanen. II Chem. Ber. 1979,112, 3041−3053.
- Dolbier Jr. W. R.- Battiste M. A. Structure, synthesis and chemical reactions of fluorinated cyclopropanes and cyclopropenes. // Chem. Rev. 2003,103, 1071−1098.
- Brahms D. L. S.- Dailey W.P. Fluorinated carbenes. // Chem. Rev. 1996, 96, 1585−1632.
- Percy J. M.- Prime M. E. Rearrangement routes to selectively fluorinated compounds. // J. Fluor. Chem. 1999,100, 147−156.
- Shi G.-q.- Wang Q.- Schlosser M. Versatile 2-fluoroacrilic building blocks for the synthesis of fluorinated heterocyclic compounds. // Tetrahedron 1996, 52, 4403−4410.
- Костиков P. P.- Хлебников А. Ф. Карбены в синтезе гетероциклов (обзор). // Химия Гетероциклических соединений 1976, 1443−1464.
- Хлебников А. Ф.- Костиков Р. Р. Иммониевые илиды из галокарбенов в синтезе азотсодержащих соединений. II Изв. Акад. Наук, сер. Химическая 1993, 646−654.
- Khlebnikov A. F.- Novikov M. S.- Kostikov R. R. Carbenes and carbenoids in synthesis of heterocycles. Adv. Heterocycl. Chem. 1996, 65, 93−233.
- Khlebnikov A. F.- Novikov M. S.- Kostikov R. R. Иминиевые илиды из карбенов и карбеноидов: генерирование и применение в синтезе. // Успехи Химии 2005, 74, 183−205.
- Костиков P.P.- Хлебников А. Ф.- Оглобин К. А. Стереоселективность присоединения несимметричных дигалокарбенов к бензилиденанилину и термическая изомеризация гел/-дигалоген-1,2-дифенилазиридинов. Докл. Акад. Наук СССР, 1975, 223, 1375−1378.
- Yamanaka Н.- Kikui J.- Teramura К.- Ando Т. Reduction of l, 3-diphenyl-2,2-dihaloaziridines with tri-n-butyltin hydride. // J. Org. Chem., 1976, 41, 3794−3797.
- Костиков P.P.- Хлебников А. Ф.- Оглобин К. А. О реакции дигалокарбенов с ароматическими азометинами. Ж. Орг. Химии 1977,13, 1857−1872.
- Khlebnikov A. F.- Novikov М. S.- Kostikov R. R. Ylides from dihalocarbenes and esters of jV-benzhydrylidene amino acids: halogen-dependent reaction pathways. Mendeleev Commun. 1997, 145−146.
- Khlebnikov A. F.- Novikov M. S.- Shinkevich E. Y.- Vidovic D. Selective transannular ring transformations in azirino-fused eight-membered 0, N- or S, N-heterocycles. // Org: Biomol. Chem. 2005, 3, 4040−4042.
- Хлебников А. Ф.- Новиков M С- Никифорова Т. Ю.- Костиков Р. Р. Реакция дигалогенкарбенов с эфирами и нитрилами iV-алкилиденаминокислот. Синтез производных аминокислот с азиридиновым и пиррольным фрагментами. // Ж. Орг. Хгшми 1999,35,98−105.
- Novikov M. S.- Khlebnikov A. F.- Besedina О. V.- Kostikov R. R. The first example of intramolecular cycloaddition of carbene-derived azomethine-ylides in a domino reaction of difluorocarbene with Schiff bases. // Tetrahedron Lett. 2001, 42, 533−535.
- Новиков M. С.- Хлебников А. Ф.- Шевченко M. В.- Костиков P. P.- Vidovic D. 1,3-Диполярное циклоприсоединение дифторзамещенных азометин-илидов. Синтез и превращения 2-фтор-2-пирролинов. //Ж. Орг. Химии 2005, 41, 1527−1537.
- Novikov М. S.- Khlebnikov A. F.- Shevchenko М. V. A facile route to 2-fluoro-2-pyrrolines via fluorinated azomethine ylides. II J. Fluor. Chem. 2003,123, 177−181.
- Novikov M. S.- Khlebnikov A. F.- Sidorina E. S.- Kostikov R. R. A facile tandem carbene-ylide route to 2-fluoropyrrole derivatives. II J. Fluor. Chem. 1998, 90, 117−119.
- Ввозный И. В.- Новиков М. С.- Хлебников А. Ф.- Kopf J.- Костиков Р. Р. Внутримолекулярное 1,3-диполярное циклоприсоединение азометин-илидов из альдиминов и дифторкарбена к сложноэфирному карбонилу. II Ж. Орг. Химии 2004, 40, 226−233.
- Новиков M. С.- Хлебников А. Ф.- Хистяев К. A.- Magull J. Изомеризация и 1,3-диполярное циклоприсоединение гем-дифторзамещенных NH-азометин-илидов в реакции дифторкарбена с диарилметаниминами. // Изв. РАН, сер. хим. 2008, 57, в печати.
- Новиков М. С.- Хлебников А. Ф.- Ввозный И. В.- Беседина О. В.- Костиков Р. Р. Внутримолекулярное 1,3-диполярное циклоприсоединение гел/-дифторазометин-илидов к кратной связи углерод-углерод. IIЖ. Орг. Химии 2005, 41, 372−380.
- Novikov М. S.- Amer A. A.- Khlebnikov A. F. Fluorinated 4//-1,3-diazepines by reaction of difluorocarbene with 2#-azirines. // Tetrahedron Lett. 2006, 47, 639−642.
- Khlebnikov A. F.- Novikov M. S.- Amer A. A. Generation and cycloadditions of azirinium difluoromethanides strained azomethine ylides. // Tetrahedron Lett. 2002, 8523−8525.
- Khlebnikov A. F.- Novikov M. S.- Amer A. A. Reaction of difluorocarbene with 2//-azirines: generation and transformations of strained azomethine ylides — aziriniodifluoromethanides. // Russ. Chem. Bull. 2004, 53, 1092−1101.
- Voznyi I. V.- Novikov M. S.- Khlebnikov A. F. Synthesis of 6,6-difluorocyclopropa6]furo[2,3-c]pyrrole and 7-fluorofuro[3,2-c]pyridine derivatives via 1,5-electrocyclisation of carbene derived azomethine ylides. // Synlett 2005, 1006−1008.
- Возный И. В.- Новиков М. С.- Хлебников А. Ф.- Костиков Р. Р. Реакции 1,5−71-циклизации гелг-дифторзамещенных азометин-илидов с участием ароматического кольца. II Ж. Орг. Химии 2006, 42, 708−714.
- Khlebnikov A. F.- Novikov M. S.- Dolgikh S. A. 1,3- vs. 1,5-cyclisation of azomethine ylides derived from l-azabuta-l, 3-dienes and difluoro- and dichlorocarbenes. Experimental and quantum-chemical study. ARKIVOC 2008, N9, 94−115.
- Huang X.-h.- He P.-y.- Shi G.-q. Highly stereoselective addition-elimination reaction of nucleophiles with ethyl 3,3-difluoro-2-(trimethylsilyl)methyl]propenoate // J. Org. Chem. 2000, 65, 627−629.
- Ernet T.- Maulitz A. H.- Wiirthwein E.-U.- Haufe G. J. Chemical consequences of fluorine substitution. Part 1. Experimental and theoretical results on Diels-Alder reactions of a- and p-fluorostyrenes. II Chem. Soc., Perkin Trans. 7 2001, 1929−1938.
- Dolbier Jr. W. R.- Rong X. X.- Bartberger M. D.- Koroniak H.- Smart B. E.- Yang Zh.-Y. Cyclization reactivities of fluorinated hex-5-enyl radicals. // J. Chem. Soc. Perkin Trans. 2 1998,219−231.
- Nair V.- Kamboj R. C. Inhibition of inosine monophosphate dehydrogenase (IMPDH) by 2−2-(Z)-fluorovinyl]inosine 5'-monophosphate. // Bioorg. Med. Chem. Lett. 2003, 13, 645−647.
- Kataoka K.- Tsuboi S. Generation of acetylides by treatment of fluoroethylenes with LDA: Preparation of propargyl alcohols. // Synthesis 1999, 452−456.
- Barkakaty B.- Takaguchi Y.- Tsuboi S. Addition of CFCI3 to aromatic aldehydes under ultrasonic irradiation. // Synthesis 2006, 959−962.
- Barhdadi R.- Simsen B.- Troupel M.- Nedelec J.-Y. Direct electroreduction or use of an electrogenerated Base: Two ways for the coupling of polyhalogenated compounds with aldehydes or ketones. // Tetrahedron 1997, 53, 1721−1728.
- Barkakaty B.- Takaguchi Y.- Tsuboi S. New synthetic routes towards various a-fluorinated aryl ketones and their enantioselective reductions using baker’s yeast. // Tetrahedron 2007, 63, 970−976.
- Nenajdenko V. G.- Shastin A. V.- Korotchenko V. N.- Varseev G. N.- Balenkova E. S. A novel approach to 2-chloro-2-fluorostyrenes. // Eur. J. Org. Chem. 2003, 302−308.
- Nenaidenko V. G.- Korotchenko V. N.- Shastin A. V.- Tyurin D. A.- Balenkova E. S. Catalytic olefination reaction of carbonyl compounds. A study on stereoselectivity of alkene formation. II Russ. Chem. Bull. 2003, 52, 1835−1840.
- Korotchenko V. N.- Shastin A. V.- Nenaidenko V. G.- Tyurin D. A.- Balenkova E. S. Reaction of catalytic olefination of hydrazones with polyhaloalkanes. Investigation of alkene formation chemoselectivity. // Russ. J. Org. Chem. 2003, 39, 527−531.
- Kvicala J.- Stambasky J.- Bohm S.- Paleta O. Equilibrium structures of isolated (halogenated) fluorolithiomethanes. II J. Fluor. Chem. 2002,113, 147−154.
- Shimizu M.- Hiyama T. Modern synthetic methods for fluorine-substituted target molecules. IIAngew. Chem. Int. Ed. 2005, 44, 214−231.
- Kvicala J.- Stambasky J.- Skalicky M.- Paleta O. Preparation of fluorohalomethylmagnesium halides using highly active magnesium metal and their reactions. // J. Fluor. Chem. 2005,126, 1390−1395.
- Kuroboshi M.- Yamada N.- Takebe Y.- Hiyama T. Generation and carbonyl addition of dibromofluoromethyllithium. // Synlett 1995, 987−988.
- Hata T.- Shimizu M.- Hiyama T. Generation and aldehyde addition of a zinc carbenoid substituted by fluorine. // Synlett 1996, 831−832.
- Hata T.- Kitagawa H.- Shimizu M.- Hiyama T. Chemoselective aldehyde addition of zinc carbenoid generated from tribromofluoromethane. // Bull. Chem. Soc. Jpn. 2000, 73, 1691−1695.
- Nakagawa M.- Saito A.- Soga A.- Yamamoto N.- Taguchi T. Chromium mediated stereoselective synthesis of (Z)-l-fluoro-2-alkenyl alkyl and trialkylsilyl ethers from dibromofluoromethylcarbinyl ethers. // Tetrahedron Lett. 2005, 46, 5257−5261.
- Shimizu M.- Takebe Y.- Kuroboshi M.- Hiyama T. Diastereoselective generation of lithium carbenoid reagent RCH (OMEM)CFBrLi and its reaction with electrophiles. // Tetrahedron Lett. 1996, 37, 7387−7390.
- Wakselman C.- Molines H.- Tordeux M. Synthesis of ethyl 3-fuoroacrylate from a Tarrant-Stump acetal. // J. Fluor. Chem. 2000,102, 211−213.
- Raju B. R.- Pramod Kumar E. K.- Saikia A. K. Palladium (0)-catalyzed addition of CFBr3 to olefins: synthesis of 1,1,3-tribromo-l-fluoroalkanes and 1,2-difluoroalkenes. // Tetrahedron Lett. 2006, 47, 9245−9248.
- Shavrin K. N.- Gvozdev V. D.- Nefedov O. M. Alkynylhalocarbenes. 4. Generation of (alk-l-ynyl)halocarbenes from 3-substituted 1,1,1,3-tetrahalopropanes under the action of bases. // Russ. Chem. Bull. 2002, 51, 1237−1253.
- Zhao G.- Yang J.- Huang W.-y. Na2S204/NaHC03-system promoted addition-cyclization of per (poly)fluoroalkyl iodides or perhaloalkanes with 1,6-heptadienes. // J. Fluor. Chem. 1997, 86, 89.
- Vanderhaar R. W .- Burton D. J .- Naae D. G. A convenient preparation of bromofluoromethylene olefins II J. Fluor. Chem. 1971/72,1, 381−383.
- Burton D. J. Preparation and synthetic utility of fluorinated phosphonium salts, bisphosphonium salts and phosphoranium salts. II J. Fluor. Chem. 1983, 23, 339−357.
- Burton D. J. Fluorinated ylides and related compounds. // Chem. Rev. 1996, 96, 1641−1715.
- Lei X .- Dutheuil G .- Pannecoucke X .- Quirion J.-C. A facile and mild method for the synthesis of terminal bromofluoroolefins via diethylzinc-promoted Wittig reaction. // Org. Lett. 2004, 6, 2101−2104.
- Zhang H .- Xu Y Zhang Z .- Liman E. R .- Prestwich G. D. Synthesis and biological activity of phospholipase C-resistant analogues of phosphatidylinositol 4,5-bisphosphate. // J. Am. Chem. Soc. 2006,128, 5642−5643.
- Xu J .- Burton D. J. Stereoselective preparation of (?) — and (Z)-a-fluorostilbenes via palladium-catalyzed cross-coupling reaction of high EIZ ratio and (Z)-1 -bromo-1 -fluoroalkenes. II J. Org. Chem. 2006, 71, 3743−3747.
- Xu J Burton D. J. Stereospecific preparation of (Z)-a-fluorostilbenes via a kinetically controlled palladium-catalyzed cross-coupling reaction of high EIZ ratio 1-bromo-1-fluorostyrenes and aryl stannanes. // Tetrahedron Lett. 2002, 43, 2877−2879.
- Chen C .- Wilcoxen K .- Strack N .- McCarthy J. R. Synthesis of fluorinated olefins via the palladium catalyzed cross-coupling reaction of 1-fluorovinyl halides with organoboranes. // Tetrahedron Lett. 1999, 40, 827−830.
- Waschbusch R.- Carran JSavignac P. A new route to a-fluorovinylphosphonates utilizing Peterson olefmation methodology. // Tetrahedron 1996, 52, 14 199−14 216.
- Zhang X.- Burton D. J. A kinetic separation method for the stereoselective preparation of a-fluorovinylphosphonates from E/Z mixtures of 1-bromo-l-fluoroolefins. // J. Fluor. Chem. 2001,772, 47−54.
- Wang Y.- Burton D. J. Base-catalyzed cyclization of monofluorodienynes: a new route to substituted fluorobenzene derivatives. // Tetrahedron Lett. 2006, 47, 9279−9281.
- Eddarir, S.- Francesch, C.- Mestdagh, H.- Rolando, C. Regio- and stereoselective synthesis of fluorinated enynes and dienes via 1,1- or 1,2-halofluoroalkenes. // Bull. Soc. Chim. Fr. 1997,134, 741−755.
- Xu J.- Burton D. J. Kinetic separation methodology for the stereoselective synthesis of (E)-and (Z)-a-fluoro-a,^-unsaturated esters via the palladium-catalyzed carboalkoxylation of1.-bromo-1 -fluoroalkenes. // Org. Lett. 2002, 4, 831−833.
- Galli C.- Guarnieri A.- Koch H.- Mencarelli P.- Rappoport Z. Effect of substituents on the structure of the vinyl radical: calculations and experiments. // J. Org. Chem. 1997, 62, 4072−4077.
- Dutheuil G.- Paturel C.- Lei X.- Couve-Bonnaire S.- Pannecoucke X. First stereospecific synthesis of (E) — or (Z)-a-fluoroenones via a kinetically controlled Negishi coupling reaction.
- J. Org. Chem. 2006, 71,4316−4319.
- Dutheuil G.- Bailly L.- Couve-Bonnaire S.- Pannecoucke X. First enantioselective reductive amination of a-fluoroenones. II J. Fluor. Chem. 2007,128, 34−39.
- Zhang X.- Burton D. J. A kinetic separation method for the stereoselective preparation of (Z) — and (7?)-monofluoroenynes from E/Z mixtures of 1-bromo-l-fluoroolefins. II J. Fluor. Chem. 2001,772,317−324.
- Xu J.- Wang Y.- Burton D. J. Site-specific preparation of 3-fluoro-l-substituted-naphthalenes via a novel base-catalyzed cyclization reaction from (?)-monofluoroenynes. // Org. Lett. 2006, «5, 2555−2558.
- Wang Y.- Xu J.- Burton D. J. A simple, two-step, site-specific preparation of fluorinated naphthalene and phenanthrene derivatives from fluorobromo-substituted alkenes. // J. Org. Chem. 2006, 77, 7780−7784.
- Saito A.- Nakagawa M.- Taguchi T. A ring-closing metathesis pathway to fluorovinyl-containing nitrogen heterocyles. // J. Fluor. Chem. 2005,126, 1166−1176.
- Eddarir S.- Abdelhadi Z.- Rolando C. Fluorinated resveratrol and pterostilbene. // Tetrahedron Lett. 2001, 42, 9127−9130.
- Shastin A.V.- Muzalevsky V. M.- Balenkova E. S.- Nenajdenko V. G. Stereoselective synthesis of 1-bromo-l-fluorostyrenes. // Mendeleev Commun. 2006, 179−180.
- Nenajdenko V. G.- Muzalevskiy V. M.- Shastin A. V.- Balenkova E. S.- Haufe G. Synthesis and Diels-Alder reactions of a-fluoro- and a-trifluoromethylacrylonitriles. // J. Fluor. Chem. 2007,128, 818−826.
- El-Khoury M.- Wang Q.- Schlosser M. A new generation of „instant ylids“: powder mixtures of phosphonium salts and potassium hydride as storable precursors to Wittig reagents. // Tetrahedron Lett. 1996, 37, 9047−9048.
- Wang Q.- Wei H.-x.- Schlosser M. The simultaneous in-situ generation of aldehydes and phosphorus ylides: a convenient multi-step one-pot olefination protocol. // Eur. J. Org. Chem. 1999, 3263−3268.
- Du Z.- Haglund M. J.- Pratt L. A.- Erickson K. L. Carbanionic rearrangements of halomethylenecyclobutanes. The role of the halogen. II J. Org. Chem. 1998, 63, 8880−8887.
- Burton D. J.- Wiemers D. M. A practical synthesis of fluoromethyltriphenylphosphonium salts. II J. Fluor. Chem. 1985, 27, 85−89.
- Inbasekaran M.- Peet N. P.- McCarthy J. R.- LeTourneau M. E. A novel and efficient synthesis of fluoromethyl phenyl sulphone and its use as a fluoromethyl Wittig equivalent. II Chem. Commun. 1985, 678−679.
- Khrimian A. P.- DeMilo A. B.- Waters R. M.- Liquido N. J.- Nicholson J. M. Monofluoro analogs of eugenol methyl ether as novel attractants for the oriental fruit fly. // J. Org. Chem. 1994, 59, 8034−8039.
- McCarthy J. R.- Matthews D. P.- Edwards M. L.- Stemerick D. M.- Jarvi E. T. A new route to vinyl fluorides. // Tetrahedron Lett. 1990, 31, 5449−5452.
- ShimizuM.- Ohno A.- Yamada S. (10Z) — and (1QE)-19-fluoro-1 a, 25-dihydroxyvitamin D3: an improved synthesis via 19-nor-10-oxo-vitamin D. // Chem. Pharm. Bull. 2001, 49, 312−317.
- Li Y.- Ni C.- Liu J.- Zhang L.- Zheng J.- Zhu L.- Hu J. Stereoselective nucleophilic monofluoromethylation of jV-(/er/-butanesulfinyl)imines with fluoromethyl phenyl sulfone. // Org. Lett. 2006, 8, 1693−1696.
- Ni C.- Li Y.- Hu J. Nucleophilic fluoroalkylation of epoxides with fluorinated sulfones. II J. Org. Chem. 2006, 71, 6829−6833.
- McCarthy J. R.- Huber E. W.- Le T.-B.- Laskovics F. M.- Matthews D. P. Stereospecific synthesis of 1-fluoro olefins via (fluorovinyl)stannanes and an unequivocal NMR method for the assignment of fluoro olefin geometry. // Tetrahedron 1996, 52, 45−58.
- Miller S. C.- McCarthy J. R.- Sabol J. S. Terminal fluoroolefins. The synthesis of novel carboacyclic nucleosides. II Nucleosides Nucleotides 1998,17, 1099−1113.
- Andrei D.- Wnuk S. F. Synthesis of the multisubstituted halogenated olefins via cross-coupling of dihaloalkenes with alkylzinc bromides. // J. Org. Chem. 2006, 71, 405−408.
- Chen C.- Wilcoxen K.- Kim K.-i.- McCarthy J. R. Palladium/copper (I) halide-cocatalyzed stereospecific coupling of 1-fluorovinylstannanes with aryl iodides and acyl chlorides. // Tetrahedron Lett. 1997, 38, 7677−7680.
- Zhang X.- Qiu W.- Burton D. J. The preparation of (Et0)2P (0)CFHZnBr and (EtO)2P (0)CFHCu and their utility in the preparation of functionalized a-fluorophosphonates. // Tetrahedron Lett. 1999, 40, 2681−2684.
- Zhang X.- Qiu W.- Burton D. J. Preparation of a-fluorophosphonates. // J. Fluor. Chem. 1998, 89, 39−49.
- Matthews D. P.- Wald P. P.- Sabol J. S.- McCarthy J. R. The synthesis of (l-fluorovinyl)tributyltin: a synthetic equivalent for the 1-fluoroethene anion. // Tetrahedron Lett. 1994, 55,5177−5180.
- Gharat L. A.- Martin A. R. Some recent results in nucleophilic trifluoromethylation and introduction of fluorinated moieties. // Heterocycles 1996, 43, 185−194.
- Hanamoto T.- Kobayashi T. Cross-coupling reactions of (l-fluorovinyl)methydiphenylsilane with aryl halides and aryl triflates. // J. Org. Chem. 2003, 68, 6354−6359.
- Hanamoto T.- Harada S.- Shindo K.- Kondo M. Fluoride ion-initiated a-fluorovinylation of carbonyl compounds with a-fluorovinyldiphenylmethylsilane. // Chem. Commun. 1999, 2397−2398.
- Hanamoto T.- Korekoda K.- Nakata K.- Handa K.- Koga Y.- Kondo M. Synthesis and reactivity of (1-fluorovinyl) phenylsulfoxide as a dienophile. // J. Fluor. Chem. 2002, 118, 99−101.
- Hanamoto T.- Shindo K.- Matsuoka M.- Kiguchi Y.- Kondo M. Synthesis and reactions of a-fluorovinylphosphonium salts. II J. Chem. Soc.- Perkin Trans. 1 2000, 103−107.
- Hanamoto T.- Kiguchi Y.- Shindo K.- Matsuoka M.- Kondo M. Preparation and synthetic applications of a-fluorovinylphosphonium salts. // Chem. Commun. 1999, 151−152.
- Hanamoto T.- Suetake T.- Koga Y.- Kawanami T.- Furuno H.- Inanaga J. Synthesis and reactions of 5-tributylstannyl-4-fluoro-l//-pyrazole. // Tetrahedron 2007, 63, 5062−5070.
- Hanamoto T.- Koga Y.- Kido E.- Kawanami T.- Furuno H.- Inanaga J. Palladium catalyzed cross-coupling reaction of 5-tributylstannyl-4-fluoropyrazole. // Chem. Commun. 2005, 2041−2043.
- Wu K.- Chen Q.-Y. Solvolitically DMSO-promoted reactions of 1,1,1-trifluoroethyl chloride (HFCC-133a) or fluoride (HFC-134a) with nucleophiles. // Tetrahedron 2002, 58, 4077−4084.
- Brown S. J.- Corr S.- Percy J. M. Fluorinated succinic acid derivatives from new refrigerants via ozonolysis of haloalkenes. // Tetrahedron Lett. 2000, 41, 5269−5273.
- Kanai M.- Percy J. M. Short, stereoselective syntheses of a-fluoroalkenoate derivatives, a-fluoroenones and a-fluoroenals from HFC-134a. // Tetrahedron Lett. 2000, 41, 2453−2455.
- Bainbridge J. M.- Corr S.- Kanai M.- Percy J. M. HFC-134a as a fluorinated building block: short syntheses of a-fluoroenones. // Tetrahedron Lett. 2000, 41, 971−974.
- Percy J. M.- Wilkes R. D. A rapid and convenient approach to functionally diverse monofluorinated vinylic compounds. // Tetrahedron 1997, 53, 14 749−14 762.
- Ichikawa J.- Fujiwara M.- Wada Y.- Okauchi T.- Minami T. The nucleophilic 5-endo-trig cyclization of gew-difluoroolefins with homoallylic functional groups: syntheses of ring-fluorinated dihydroheteroaromatics.// Chem. Commun. 2000, 1887−1888.
- Amin M. R.- Harper D. B.- Moloney J. M.- Murphy C. D.- Howard J. A. K. O’Hagan D. A short highly stereoselective synthesis of the fluorinated natural product (2S, 3S)-4-fluorothreonine. // Chem. Commun. 1997, 1471−1472.
- Zhang H.-Z.- Rao K.- Carr S. F.- Papp E.- Straub K.- Wu J. C.- Fried J. Rationally designed inhibitors of inosine monophosphate dehydrogenase. // J. Med. Chem. 1997, 40, 4−8.
- Myers A. G.- McKinstry L.- Barbay J. K.- Gleason J. L. Practical methodology for the asymmetric synthesis of organofluorine compounds. // Tetrahedron Lett. 1998, 39, 1335−1338.
- Huang X.-T.- Chen Q.-Y.- Ethyl a-fluoro silyl enol ether: stereoselective synthesis and its aldol reaction with aldehydes and ketones. II J. Org. Chem. 2002, 67, 3231−3234.
- Ocampo R.- Dolbier W. R. Jr.- Abboud K. A.- Zuluaga F. Catalyzed Reformatsky reactions with ethyl bromofluoroacetate for the synthesis of a-Fluoro-/?-hydroxy acids. // J. Org. Chem. 2002, 67, 72−78.
- Katritzky A. R.- Nichols D. A.- Qi M. Benzotriazole mediated syntheses of a-fluoro-p-amino esters. // Tetrahedron Lett. 1998, 39, 7063−7066.
- Wilde J.- Eggerer H. Differential recognition of chirality at C-2 of 2-fluoro- and2. methylmevalonate by mevalonate kinase absolute configuration of enzymatically active 2-fluoromevalonate. // Liebigs Ann. 1997, 581−585.
- Qiu Y.- Li D. Inhibition of mevalonate 5-diphosphate decarboxylase by fluorinated substrate analogs. // Biochim. Biophys. Acta 2006,1760, 1080−1087.
- Inagaki H.- Sugita K.- Miyauchi R. N.- Miyauchi S.- Takeda T.- Itoh M.- Takahashi H.- Takemura M. Improved synthesis of DQ-113, a new quinolone antibacterial agent, utilizing the Reformatsky reaction. // ARKIVOC 2003, 112−117.
- Long Z.-Y.- Chen Q. Y. The activation of carbon-chlorine bonds in per- and polyfluoroalkyl chlorides: DMSO-induced hydroperfluoroalkylation of alkenes and alkynes with sodium dithionite. II J. Org Chem. 1999, 64, 4775−4782.
- Jean-Baptiste L.- Yemets S.- Legay R.- Lequeux T. Synthesis of 2,3-trans disubstituted tetrahydrofurans through sequential xanthate radical addition-substitution seactions. // J. Org Chem. 2006, 71, 2352−2359.
- Wang Y.- Yang Z.-Y.- Burton D. J. Nickel catalyzed reaction of iodofluoroacetates with alkenes as a facile route to a-fluoroesters. // Tetrahedron Lett. 1992, 33, 2137−2140.
- Zhi C.- Chen Q. Y. Novel and practical preparation of a-fluoro-functionalized esters from fluoroiodoacetates. II J. Chem. Soc.- Perkin Trans. 1 1996, 1741−1747.
- Saito A.- Ito H.- Taguchi T. A stereoselective preparation of 1-fluorocyclopropane-l-carboxylate derivatives through radical addition of fluoroiodoacetate to alkenes followed by intramolecular substitution reaction. // Tetrahedron 2001, 57, 7487−7493.
- Takeuchi Y.- Kirihara K.- Kirk K. L.- Shibata N. Synthesis of carbonyl-bridged peptides containing an a-fluoroglycine residue. // Chem. Commun. 2000, 785−786.
- Takeuchi Y.- Kamezaki M.- Kirihara K.- Haufe G.- Laue K. W.- Shibata N. Chemistry of a-fluoro-a-aminoacids: the first synthesis of a-fluoroglycine-containing dipeptides. // Chem. Pharm. Bull. 1998, 46, 1062−1064.
- Annedi S. C.- Li W.- Samson S.- Kotra L. P. Design and synthesis of novel fluoropeptidomimetics as potential mimics of the transition state during peptide hydrolysis. II J. Org Chem. 2003, 68, 1043−1049.
- Verniest G.- Colpaert F.- Van Hende E.- De Kimpe N. Synthesis and reactivity of 1-substituted 2-fluoro- and 2,2-difluoroaziridines. II J. Org. Chem. 2001, 72, 8569−8572.
- Choudary B. M.- Mahendar K.- Kantam M. L.- Ranganath K. V. S.- Athar T. The one-pot Wittig reaction: a facile synthesis of a,|3-unsaturated esters and nitriles by using nanocrystalline magnesium oxide. II Adv. Synth. Catal. 2006, 348, 1977−1985.
- Falck J. R.- Bejot R.- Barma D. K.- Bandyopadhyay A.- Joseph S.- Mioskowski C. Fe (0)-mediated synthesis of tri- and tetra-substituted olefins from carbonyls: an environmentally friendly alternative to Cr (II). II J. Org. Chem. 2006, 71, 8178−8182.
- Barma D. K.- Kundu A.- Zhang H.- Mioskowski C.- Falck J. R. (Z)-a-Haloacrylates: an exceptionally stereoselective preparation via Cr (II)-mediated olefination of aldehydes with trihaloacetates. II J. Am. Chem. Soc. 2003,125, 3218−3219.
- Khambay B. P. S.- Farnham A. W.- Liu M. G. The pyrethrins and related compounds. Part XLII: Structure-activity relationships in fluoro-olefin non-ester pyrethroids. // Pestic. Sci. 1999, 55, 703−710.
- Iseki K.- Kuroki Y.- Kobayashi Y. Enantioselective aldol reaction with a bromofluoroketene silyl acetal catalyzed by a chiral Lewis acid. // Tetrahedron Lett. 1997, 38, 7209−7210.
- Iseki K.- Kuroki Y.- Kobayashi Y. Enantioselective aldol reaction with bromofluoroketene silyl acetals. // Tetrahedron 1999, 55, 2225−2236.
- Mima K.- Ishihara Т.- Kuwahata S.- Konno Т.- Yamanaka H. Highly stereoselective radical reduction of a-bromo-a-fluoro-p-hydroxy esters with tributyltin hydride leading to threo-a-fluoro-p-hydroxy esters. // Chem. Lett. 2002, 192−193.
- Zoute L.- Lacombe C.- Quirion J.-C.- Charette А. В.- Jubault P. Phosphonium supported triphenylphosphine reagent: an improved access to a-fluoro-a, P-unsaturated esters. // Tetrahedron Lett. 2006, 47, 7931−7933.
- Sano S.- Teranishi R.- Nagai Y. Toward (Z)-selective Horner-Wadsworth-Emmons reaction of aldehydes with 2-fluoro-2-diethylphosphonoacetic acid. // Tetrahedron Lett. 2002, 43, 9183−9186, см. также цитируемую лит.
- Kim A.- Hong J. H. Synthesis and antiviral activity of C-fluoro-branched cyclopropyl nucleosides. II Eur. J. Med. Chem. 2007, 42, 487−493.
- Engman M.- Diesen J. S.- Paptchikhine A.- Andersson P. G. Iridium-catalyzed asymmetric hydrogenation of fluorinated olefins using N, P-ligands: a struggle with hydrogenolysis and selectivity. II J. Am. Chem. Soc. 2007,129, 4536−4537.
- Hong H. J.- Kim H. O.- Moon H. R.- Jeong L. S. Synthesis and antiviral activity of fluoro-substituted apio dideoxynucleosides. II Arch. Pharm. Res. 2001, 24, 95−99.
- Sano S.- Kuroda Y.- Saito K.- Ose Y.- Nagao Y. Tandem reduction-olefmation of triethyl 2-acyl-2-fluoro-2-phosphonoacetates and a synthetic approach to Cbz-Gly-T (Z)-CF=C]-Gly dipeptide isostere. // Tetrahedron 2006, 62, 11 881−11 890.
- Deng G. S.- Liu C. Y. One-pot approach to the conversion of alcohols into a-halo-a, 3-unsaturated esters. // Chinese Chem. Lett. 2006,17, 329−332.
- Raju В.- Anandan S.- Gu S.- Herradura P.- O’Dowd H.- Kim В.- Gomez M.- Hackbarth C.- Wu C.- Wang W.- Yuan Z.- White R.- Trias J.- Patel D. V. Conformationally restricted analogs of deoxynegamycin. // Bioorg. Med. Chem. Lett. 2004,14, 3103−3107.
- Tsai H.-J. Isolation and characterization of intermediate in the synthesis of a-fluorodiesters. II J. Chinese Chemical Society 1998, 45, 543−548.
- Sano S.- Yokoyama K.- Shiro M.- Nagao Y. A facile method for the stereoselective Horner-Wadsworth-Emmons reaction of aryl alkyl ketones. // Chem. Pharm. Bull. 2002, 50, 706−709.
- Machleidt H.- Wessendorf R. Organische Fluoroverbindungen, IV. Carbonyl-fluorolefinierungen. //Ann. Chem.- 1964, 674, 1−10.
- Kiddle J. J.- Gurley A. F. Microwave irradiation in organophosphorus chemistry 1: the Michaelis-Arbuzov reaction. 11 Phosphorus Sulfur 2000,160, 195−205.
- А. Ф. Фокин- В. И. Зимин- Ю. Н. Студнев- А. И. Рапкин Некоторые реакции производных фторхлоруксусной кислоты с нуклеофильными реагентами. // Ж. Орг. Химии 1971, 7,249−251.
- Waschbusch R.- Carran J.- Savignac P. New routes to diethyl 1-fluoromethylphosphonocarboxylates and diethyl 1-fluoromethylphosphonocarboxylic acid. // Tetrahedron 1997, 53, 6391−6400.
- Kvicala J.- Vlasakova R.- Plocar J.- Paleta O.- Pelter A. Preparation of intermediates for fluorinated lignans by conjugated and tandem additions on 3-fluorofuran-2-(5//)-one. // Collect. Czech. Chem. Commun. 2000, 65, 772−788.
- Sano S.- Saito K.- Nagao Y. Tandem reduction-olefination for the stereoselective synthesis of (Z)-a-fluoro-a, p-unsaturated esters. // Tetrahedron Lett. 2003, 44, 3987−3990.
- Park J.-H.- Choi M.-H.- Jeong L. S.- Chun M. W.- Kim H. D. Synthesis of r-Fluoro-2', 2'-bis-(hydroxymethyl)-cyclopropylmethyl]purines as antiviral agents. // Nucleos. Nucleot. Nucl. Acids 2003, 22, 955−957.
- Shinada T.- Sekiya N.- Bojkova N.- Yoshihara K. Stereoselective synthesis of 9-/ram,-9-desmethyl-9-fluororetinals based on the four-components coupling approach. // Tetrahedron 1999, 55, 3675−3686.
- Percy E.- Singh M.- Takahashi T.- Takeuchi Y.- Kirk K. L. Synthesis of E- and Z-a-fluorourocanic acids as potential inhibitors of urocanase. // J. Fluor. Chem. 1998, 91, 5−7.
- Kim B. T.- Min Y. K.- Asami T.- Park N. K.- Kwon O. Y.- Cho K. Y.- Yoshida S. 2-Fluoroabscisic acid analogues: their synthesis and biological activities. // J. Agric. Food Chem. 1999, 47, 313−317.
- Sano S.- Yokoyama K.- Teranishi R.- Shiro M.- Nagao Y. Enantioselective Horner-Wadsworth-Emmons reaction for the asymmetric synthesis of a-fluoro-a, p-unsaturated esters. // Tetrahedron Lett. 2002, 43, 281−284.
- Kim D. Y.- Rhie D. Y.- Oh D. Y. Acylation of diethyl (ethoxycarbonyl)fluoromethylphosphonate using magnesium chloride-triethylamine: a facile synthesis of a-fluoro (3-keto esters. // Tetrahedron Lett. 1996, 37, 653−654.
- Kim D. Y.- Lee Y. M.- Choi Y. J. Acylation of a-fluorophosphonoacetate derivatives using magnesium chloride-triethylamine. // Tetrahedron 1999, 55, 12 983−12 990.
- Yoshimatsu M.- Murase Y.- Itoh A.- Tanabe G.- Muraoka O. Z-Selective or stereospecific alkenylation reaction: a novel synthetic method for a-fluoro-a, p-unsaturated esters. // Chem. Lett. 2005, 34, 998−999.
- De Matteis V.- van Delft F. L.- Tiebes J.- Rutjes F. P. J. T. A ring-closing metathesis pathway to fluorovinyl-containing nitrogen heterocyles. // Eur. J. Org. Chem. 2006, 1166−1176.
- Laue K. W.- Haufe G. 3-Bromo-2-fluoropropene a fluorinated building block. 2-Fluoroallylation of glycine and alanine ester imines. // Synthesis, 1998, 1453−1456.
- Bravo P.- Frigerio M.- Ono T.- Panzeri W.- Pesenti C.- Sekine A.- Viani F. Synthesis of 2-fluoro analogues of frontalin. II Eur. J. Org. Chem. 2000, 1387−1389.
- Zhang F.- Song Z. J.- Tschaen D.- Volante R. P. Enantioselective preparation of ring-fused 1-fluorocyclopropane-l-carboxylate derivatives: en route to mGluR 2 receptor agonist MGS0028. // Org. Lett. 2004, 6, 3775−3777.
- Delarue-Cochin S.- Bahlaouan B.- Hendra F.- Ourevitch M.- JosephD.- Morgant G.- Cave C. Stereocontrolled access to a-fluoro-?-ketoesters. // Tetrahedron-Asymmetry 2007, 18, 759−764.
- Meyer O. G. J.- Frohlich R.- Haufe G. Asymmetric cyclopropanation of vinyl fluorides: access to enantiopure monofluorinated cyclopropane carboxylates. // Synthesis 2000, 1479−1490.
- Wong A.- Welch C. J.- Kuethe J. T.- Vazquez E.- Shaimi M.- Henderson D.- Davies I. W.- Hughes D. L. Reactive resin facilitated preparation of an enantiopure fluorobicycloketone. // Org. Biomol. Chem. 2004, 2, 168−174.
- Guseva E. V.- Volchkov N. V.- Tomilov Y. V.- Nefedov O. M. Catalytic cyclopropanation of fluorine-containing alkenes and dienes with diazomethane and methyl diazoacetate. // Eur. J. Org. Chem. 2004, 3136−3144.
- Lin W.- Charette A. B. Rhodium-catalyzed asymmetric intramolecular cyclopropanation of substituted allylic cyanodiazoacetates. II Adv. Synth. Catal. 2005, 347,1547−1552.
- Cheng D.- Kreethadumrongdat Т.- Cohen T. Allylic lithium oxyanionic directed and facilitated Simmons-Smith cyclopropanation: stereoselective synthesis of (±)-cw-sabinene hydrate and a novel ring expansion. // Org. Lett. 2001, 3, 2121−2123.
- Hruschka S.- Frohlich R.- Kirsch P.- Haufe G. Synthesis of new enantiopure fluorinated phenylcyclopropanecarboxylates potential chiral dopants for liquid-crystal compositions. II Eur. J. Org. Chem. 2007, 141−148.
- Rosen T. C.- Yoshida S.- Frohlich R.- Kirk K. L.- Haufe G. Fluorinated phenylcyclopropylamines. 2. Effects of aromatic ring substitution and of absolute configuration on inhibition of microbial tyramine oxidase. // J. Med. Chem. 2004, 47, 5860−5871.
- Haufe G.- Rosen Т. C.- Meyer O. G. J.- Frohlich R.- Rissanen K. Synthesis, reactions and structural features of monofluorinated cyclopropanecarboxylates. // J. Fluor. Chem. 2002, 114, 189−198.
- Usuki Y.- Fukuda Y.- Iio H. 2-Еthoxycarbonyl-2-fluoroaziridines: methylene-bridged (Ca to N) a-fluoro-a-aminoacids analogues. // ITE letters on Batteries, New Technologies and Medicine, 2001, 2, 237−240 (Chem. Abstr.: 2001,136, 184 068).
- Gauzy C.- Saby В.- Pereira E.- Faure S.- Aitken D. J. The 2+2] photocycloaddition of uracil derivatives with ethylene as a general route to c/s-cyclobutane ?-amino acids. // Synlett 2006, 1394−1398.
- Ohkura K.- Ishihara Т.- Nishijima K.-i.- Diakur J. M.- Seki K.-i. Stereoselective synthesis of tetrahydronaphthocyclobutal, 2-?/]pyrimidindiones from 5-fluoro-l, 3-dimethyluracyl and naphthalenes. // Chem. Pharm. Bull. 2005, 53, 258−259.
- Ohkura K.- Sugaoi Т.- Ishihara Т.- Seki K.-i. Mode switching during the cycloaddtion of 5-fluoro-l, 3-dimethyluracile wuth naphthalene from 1,4- to 1,2-addition. // Heterocycles 2004, 64, 57−60.
- Fang X.- Wu Y.-M.- Deng J.- Wang S. W. Synthesis of monofluorinated indolizines and their derivatives by the 1,3-dipolar reaction of ALylides with fluorinated vinyl tosylates. // Tetrahedron 2004, 60, 5487−5493.
- Wu K.- Chen Q.-Y. A facile synthetic method for 2-fluoroindolizines from 1 -chloro-2,2,2-trifluoroethane (HCFC-133a) and 1,1,1,2-tetrafluoroethane (HFC-134a). II J. Fluor. Chem. 2003,122, 171−174.
- Ю. А. Котикян, Б. JI. Дяткин, Ю. С. Константинов Этил-а-фторакрилат в реакциях диенового синтеза и циклоприсоединения. II Изв. Акад. Наук СССР, Серия Хим. 1971, 358−362.
- Ito H.- Saito A.- Taguchi T. Asymmetric Diels-AIder reactions of 2-fluoroacryIic acid derivatives. Part 1: the construction of fluorine substituted chiral tertiary carbon. // Tetrahedron: Asymmetry 1998, 9, 1979−1987.
- Ito H.- Saito A.- Kakuuchi A.- Taguchi T. Synthesis of 2-fluoro analog of 6-aminonorbornane-2,6-dicarboxylic acid: a conformationally rigid glutamic acid derivative. // Tetrahedron 1999, 55, 12 741−12 750.
- Essers M.- Miick-Lichtenfeld C.- Haufe G. Diastereoselective Diels-Alder reactions of a-fluorinated a./?-unsaturated carbonyl compounds: chemical consequences of fluorine substitution. II J. Org. Chem. 2002, 67, 4715−4721.
- Essers M.- Ernet T.- Haufe G. Enantioselective Diels-Alder reactions of a-fluorinated a, P-unsaturated carbonyl compounds. Part 5. Chemical consequences of fluorine substitution. II J. Fluor. Chem. 2003,121, 163−170.
- Saito A.- Yanai H.- Sakamoto W.- Takahashi K.- Taguchi T. Intramolecular Diels-Alder reaction of a-fluoroacrylate derivatives promoted by novel bidentate aluminum Lewis acid. II J. Fluor. Chem. 2005,126, 709−714.
- Gorgues A.- Stephan D.- Cousseau J. Mono-hydrofluorination of electrophilic alkynes by the liquid biphasic CSF-H2O-DMF system (DMF = AyV-dimethylformamide). // Chem. Commun. 1989, 1493−1494.
- Crowley P. J.- Percy J. M.- Stansfield K. Synthesis and reactivity of a fluorinated dienophile. // Tetrahedron Lett. 1996, 37, 8237−8240.
- Ernet T.- Haufe G. Diels-Alder reactions of vinyl fluorides with 1,3-diphenylisobenzofuran. // Tetrahedron Lett. 1996, 37, 7251−7252.
- Sridhar M.- Krishna K. L.- Rao J. M. Synthesis and Diels-Alder cycloaddition reactions of (2,2-dichloro-l-fluoroethenyl)sulfinyl] benzene and [(2-chloro-l, 2-difluoro ethenyl) sulfinyl] benzene. // Tetrahedron 2000, 56, 3539−3545.
- Ohkura K.- Kudo M.- Ishihara T.- Nishijima K.-i.- Seki K.-i. Photochemical synthesis of benzopyrimidosemibullvalenes from benzopyrimidobarrellenes. // Heterocycles 2005, 65, 2583−2586.
- Ohkura K.- Ishihara Т.- Nishijima K.-i.- Diakur J. M.- Seki K.-i. Synthesis of M, AG-free pyrimidine bridged polycyclic compounds via photo Diels-Alder reaction of 7V», iV-diacetyl-5-fluorouracil with naphthalenes. // Heterocycles 2006, 69, 515−520.
- Ohkura K.- Sugaoi Т.- Sakushima A.- Nishijima K.-i.- Kuge Y.- Seki K.-i. Thermodynamically-controlled photocycloaddition of 5-fluoro-l, 3-dimethyluracil to naphthalenes. // Heterocycles 2002, 58, 595−600.
- Ohkura K.- Sugaoi Т.- Nishijima K.-i.- Kuge Y.- Seki K.-i. Stereoselective synthesis of 4a-fluoro-5,10-ethenobenzo/]quinazolines via photo-Diels-Alder reaction of 5-fluoro-l, 3-dimethyluracil with naphthalenes. // Tetrahedron Lett. 2002, 43, 3113−3115.
- Jeong I. H.- Kim Y. S.- Cho K. Y. Unexpected effect of fluorine in Diels-Alder reaction of 2-fluoroacrolein with thebaine. II Bull. Korea Chem. Soc. 1990,11, 178−179.
- Gu Y.- Hama Т.- Hammond G. B. Diastereoselective synthesis of cyclic a-fluoromethylidenephosphonates using a-fluoroallenephosphonate as dienophile. // Chem. Commun. 2000, 395−396.
- Patrick Т. В.- Rogers J.- Gorrell K. A convenient preparation of 2-fluoro-3-alkoxy-1,3-butadienes. // Org. Lett. 2002, 4, 3155−3156.
- Patrick Т. В.- Gorrell K.- Rogers J. Microwave assisted Diels-Alder cycloaddition of 2-fluoro-3 -methoxy-1,3-butadiene. II J. Fluor. Chem. 2007,128, 710−713.
- Dmowski W.- Manko V. A.- Nowak I. 3-Chloro-4-fluorothiophene-l, l-dioxide. A new synthetically useful fluorodiene. II J. Fluor. Chem. 1998, 88, 143−151.
- Patrick Т. В.- Yu H.- Taylor D.- Gorrell K. A fluorinated masked o-benzoquinone. // J. Fluor. Chem. 2004, 125, 1965−1966.
- Muller G. H.- Lang A.- Seithel D. R.- Waldmann H. An enzyme-initiated hydroxylation -oxidation carbo Diels-Alder domino reaction. // Chem. Eur. J. 1998, 4, 2513−2522.
- Fritz H. P.- Kornrumpf W. Z. Z. Die Reduktion von CBr2F2 durch Blei ein neuartiger Weg zum Difluorocarben. // Z. Naturforsch, 1981, 36b, 1375.
- Хлебников А. Ф.- Никифорова Т. Ю.- Костиков Р. Р. Реакции азометин-илидов из дихлоркарбена и ациклических и циклических N-алкилиминов. IIЖ. Орг. Химии 1996, 32, 746−760.
- Tsuge О.- Ueno К.- Kanemasa S.- Yorozu К. Stereoselectivity of cycloaddition of Ar-(cyanomethyl) — and 7V-(a-cyanobenzyl)imines with oleflnic dipolarophiles. // Bull. Chem. Soc. Japan, 1986,59, 1809−1824.
- AsakuraN.- Usuki Y.- Iio H. A new synthesis of a-fluorovinylsulfones utilizing the Peterson olefination methodology. II J. Fluor. Chem. 2003,124, 81−88.
- Fluoroolefins. VII. Preparation of terminal vinyl fluorides. // J. Org. Chem. 1975, 40, 2796
- Hata Y.- Watanabe M. Fragmentation reaction of aziridinium ylids. // Tetrahedron Lett. 1972, 3827−2830.
- Van Hende, E.- Verniest, G.- Surmont, R.- De Kimpe, N. Synthesis of 3-substituted 2-fluoro-and 2,2-difluoroaziridines. // Organic Letters, 2007, 9, 2935−2937.
- Bjorgo J.- Boyd D. R.- Watson C. G.- Jennings W. B. Equilibrium distribution of E-Z ketimine isomers. // J. Chem. Soc., Perkin 2 1974, 757−762.
- Костиков P. P.- Хлебников А. Ф.- Оглобин К. А. Термическая изомеризация 3,3-дигалоген-1,2-дифенилазиридинов. // Химия Гетероциклических Соединений, 1978,1, 48−53.
- Govande V. V.- Deshmukh A. R. A. S. Facile stereoselective synthesis of l, 3-disubstituted-4-trichloromethyl azetidin-2-ones. Tetrahedron Lett. 2004,45, 6563−6566.
- Petasis, N. A.- Akritopoulou, I. The boronic acid Mannich reaction: a new method for the synthesis of geometrically pure allylamines. // Tetrahedron Lett. 1993, 34, 583−586.
- Petasis, N. A.- Zavialov, I. A. A new and practical synthesis of a-amino acids from alkenyl boronic acids. II J. Am. Chem. Soc. 1997, 119, 445−446.
- Grigg, R.- Sridharan, V.- Thayaparan, A. Synthesis of novel cyclic a-amino acid derivatives via a one-pot sequential Petasis reaction/palladium catalysed process. // Tetrahedron Lett. 2003,44, 9017−9019.
- Petasis, N. A.- Zavialov, I. A. Highly stereocontrolled one-step synthesis of anti-fi-amino alcohols from organoboronic acids, amines, and a-hydroxy aldehydes. // J. Am. Chem. Soc. 1998,120, 11 798−11 799.
- Petasis, N. A.- Goodman, A.- Zavialov, I. A. A new synthesis of a-arylglycines from aryl boronic acids. Tetrahedron 1997, 53, 16 463−16 470.
- Petasis, N. A.- Boral, S. One-step three-component reaction among organoboronic acids, amines and salicylaldehydes. // Tetrahedron Lett. 2001, 42, 539−542.
- Jiang, В.- Yang, C. G.- Gu, X. H. A highly stereoselective synthesis of indolyl TV-substituted glycines. // Tetrahedron Lett. 2001, 42,2545−2547.
- Веггёе, F.- Debache, A.- Marsac, Y.- Carboni, B. A new access to 2-hydroxymorpholines through a three-component Petasis coupling reaction. // Tetrahedron Lett. 2001, 42, 3591−3594
- Portlock, D. E.- Naskar, D.- West, L.- Li, M. Petasis boronic acid-Mannich reactions of substituted hydrazines: synthesis of a-hydrazinocarboxylic acids. // Tetrahedron Lett. 2002, 43, 6845−6847.
- Schlienger, N.- Bryce, M. R.- Hansen, Т. K. Heterocyclic aldehydes as novel components in the boronic Mannich reaction. // Tetrahedron Lett. 2000, 41, 1303−1305.
- Jourdan, H.- Gouhier, G.- Van Hijfte, L.- Angibaud, P.- Piettre, S. R. On the use of boronates in the Petasis reaction. // Tetrahedron Lett. 2005, 46, 8027−8031.
- Stas S., Tehrani K. A. Novel boronic acid Mannich reactions of a, a-dichloro- and a, a, co-trichloroaldehydes with arylboronic acids. // Synthesis 2007, 3, 433−441.
- S. Stas, K. A. Tehrani, Lewis acid promoted Mannich type reactions of a, a-dichloroaldimines with potassium organotrifluoroborates. // Tetrahedron 2007, 63, 8921−8931.
- Billard, Т.- Langlois, B. R. Reactivity of stable trifluoroacetaldehyde hemiaminals. 2. Generation and synthetic potentialities of fluorinated iminiums. // J. Org. Chem. 2002, 67, 997−1000.
- Seyferth D.- Hopper S.P. Halomethyl-metal compounds: LXI. Phenyl (fluorodibromomethyl)mercury, a fluorobromocarbene precursor. J. Organomet. Chem. 1973, 51,77−87.
- M.J. O’Donnell, R.L. Polt A mild and efficient route to Schiff base derivatives of amino acids. II J. Org. Chem. 1982, 47, 2663−2666.
- Padwa A.- Bergwark W.- Pashayan D. Mechanism of the photoreduction of N-alkylbenzylidene imines. И J. Am. Chem. Soc. 1969, 91, 2653−2660.
- Шкляев В. С.- Александров Б. Б.- Вахрин М. И.- Леготкина Г. И. Синтез енаминов -производных 3,4-дигидроизохинолина. II Хим. Гетероцикл. Соед. 1983, № 11, 1560.
- Jilek J. О.- Pomykace J.- Metisova J.- Metys J.- Protiva M. Neutrope und psychotrope Substanzen. 3. Derivate des Dibenz6,/][l, 4]oxazepins. // Collect. Czech. Chem. Commun. 1965, JO, 463−473.
- Taylor R. С.- McKillop A.- Hawks G. H. Diphenylketene. // Organic synthesis. An annual publication of satisfactory methods for preparation of organic chemicals. 1972, Vol. 52., J. Wiley & Sons. p. 36−38.
- Molander, G. A.- Katona, B. W.- Maehrouchi, F. Development of the Suzuki-Miyaura cross-coupling reaction: use of air-stable potassium alkynyltrifluoroborates in aryl alkynylations. II J. Org. Chem. 2002, 67, 8416−8423.
- Органикум. Практикум по органической химии. Ч. 2.- с. 103, «Мир», Москва, 1979.
- Yamanaka, Н.- Kikui, J.- Teramura, К. Reduction of l, 3-diphenyl-2,2-dihaloaziridines with tri-n-butyltin hydride. II J. Org. Chem. 1976, 41, 3794−3797.
- Фаворская И. А.- Ремизова JI. А. К вопросу о синтезе ЛГ-фенилцистеина. II Ж. Орг. Химии, 1953, 23, 667−670.
- Eckstein Z., Jelenski P., Kowal J., Rusek D. A convenient procedure for diphenylacetamide derivatives preparation. // Synth. Commun. 1982,12, 201−208.
- Hannam J.S., Lacy S.M., Leigh D.A., Saiz C.G., Slawin A.M.Z., Stitchell S.G. Controlled submolecular translation motion in synthesis: a mechanically interlocking auxilliary. // Angew. Chem. Int. Ed. 2004, 25, 3260−3264.
- Sheehan C., Bloom B.M. The synthesis of teloidinone and 6-hydroxytropinone. // J. Am. Chem. Soc. 1952, 74, 3825−3828.