Синтез имидазолийсодержащих ?-аминокислот в энантиомерно чистой форме и их использование в качестве органокатализаторов и лигандов для металлокомплексных каталитических систем
Диссертация
Современный органический синтез подразумевает не только эффективное проведение реакций для образования требуемого углеродного скелета молекулы, но и получение строго заданной абсолютной конфигурации атомов в скелете молекулы. Возрастание во всём мире интереса к асимметрическим методам синтеза энантиомерно чистых соединений связано с их практической ценностью, в основном как компонентов… Читать ещё >
Содержание
- I. Введение
- II. Литературный обзор
- 11. 1. Органические ионные жидкости
- 11. 2. Карбеновые комплексы металлов
- 11. 3. Асимметрический синтез а-аминокислот
- II. 3.1. СТЕХИОМЕТРИЧЕСЖЙ АСИММЕТРИЧЕСКИЙ СИНТЕЗ АМИНОКИСЛОТ
- III. Постановка задачи
- IV. Результаты и обсуждение
- IV. 1. Получение аминокислот, содержащих заряженный имидазолиевый фрагмент в боковой цепи
- IV. 2. Катализ с использованием карбеновых комплексов серебра
- IV. 3. Использование оснований Шиффа имидазолийсодержащих аминокислот в качестве лигандов в металлокомплексном катализе
- IV. 4. Использование цвиттерионых производных аминокислот в качестве органокатализаторов
- IV. 5. Использование цвиттерионных производных имидазолсодержащих аминокислот в качестве межфазных преносчиков
- IV. 6. Использование цвиттерионных производных имидазолсодержащих аминокислот в качестве оснований
- V. Выводы
- VI. Экспериментальная часть
Список литературы
- T. Welton, Chem. Rev., 1999, 99, 2071. «Room-temperature ionic liquids. Solvents for synthesis and catalysis».
- N. V. Plechkova, K. R. Seddon, Chem. Soc. Rev., 2008, 37, 123. «Applications of ionic liquids in the chemical industry».
- M.J. Cannarsa., Chemistry & Industry, 1996, 374. «Single enantiomer drugs: new strategies and directions».
- A.M. Rouhi, Chem. Eng. News., 2003, 18, 56. «Chirality at work».
- Д.Р. Лоуренс, П. Н. Бенетт. «Клиническая фармакология». Медицина: Москва 1993.
- March J., Advanced Organic Chemistry- Mc-Graw-Hill: New York, 1977- pp 106−108.
- D. Seebach, H. A. Oei, Angew. Chem., Int. Ed. Engl., 1975, 14, 634. «Mechanism of Electrochemical Pinacolization. The First Asymmetric Synthesis in a Chiral Medium».
- J.-C. Plaquevent, J. Levillain, F. Guillen, C. Malhiac, A.-C. Gaumont., Chem. Rev. 2008, 108, 5035. «Ionic Liquids: New Targets and Media for r-Amino Acid and Peptide Chemistry».
- K. Bica, P. Gaertner., Eur. J. Org. Chem., 2008, 3235. «Application of chiral ionic liquids»
- A. Winkel, R. Wilhelm., Tetrahedron: Asymmetry, 2009, 20, 2344. «New chiral ionic liquids based on imidazolinium salts».
- X. Chen, X. Li, A. Hu, F. Wang., Tetrahedron: Asymmetry, 2008, 19, 1. «Advances in chiral ionic liquids derived from natural amino acids».
- A. J. Arduengo, R. L. Harlow, M. K. Kline, J. Am. Chem. Soc., 1991, 113, 361. «А stable crystalline carbene».
- D. Borissou, O. Guerret, F. P. Gabai., G. Bertrand, Chem. Rev., 2000, 100, 39. «Stable Carbenes».
- W. A. Herrmann, Angew. Chem. Int. Ed., 2002, 41, 1290. «N-Heterocyclic Carbenes: A NewConcept in Organometallic Catalysis».
- D. Enders, O. Niemeier, A. Henseler, Chem. Rev., 2007, 107, 5606. «Organocatalysis by N-Heterocyclic Carbenes».
- K.M. Hindi, M.J. Panzner, C.A. Tessier, C.L. Cannon, W.J. Youngs, Chem. Rev. 2009, 109, 3859. «The Medicinal Applications of Imidazolium Carbene-Metal Complexes».
- S. Ray, R. Mohan, J.K. Singh, M.K. Samantaray, M.M. Shaikh, D. Panda, P. Ghosh, J. Am. Chem. Soc., 2007, 129, 15 042. «Anticancer and Antimicrobial Metallopharmaceutical Agents Based on Palladium, Gold, and Silver N-Heterocyclic Carbene Complexes».
- S. Gabriel, J. Weiner. Chem. Ber. 1888, 21, 2669. «Ueber einige Abkommlinge des Propylamins».
- P. Waiden, Bull.Acad.Imper.Sci.(St. Petersburg), 1914, 1800. «Molecular weights and electrical conductivity of several-fused salts».
- H. Olivier-Bourbigou, L. Magna, J. Mol. Cat. A.: Chemical., 2002, 182−183, 419. «Ionic liquids: perspectives for organic and catalytic reactions».
- David A. Jaeger, Charles E. Tucker, Tetrahedron: letters, 1989, 30, 14, 1785. «Diels-Alder reactions in ethylammonium nitrate, a low-melting fused salt».
- T. Fischer, A. Sethi, T. Welton, J. Woolf, Tetrahedron: Letters, 1999, 40, 793. «Diels-Alder reactions in room-temperature ionic liquids».
- C. Wheeler, K.N. West, C.L. Liotta, C.A. Eckert, Chem. Commiin., 2001, 887. «Ionic liquids as catalytic green solvents for nucleophilic displacement reactions».
- M.J. Earle, P.B. McCormac, K.R. Seddon, Green Chemistry, 2000, 2, 261. «The first high yield green route to a pharmaceutical in a room temperature ionic liquid».
- M.J. Earle, P.B. McCormac, K.R. Seddon, Chem. Commun., 1998, 2245. «Regioselective alkylation in ionic liquids».
- S. H. Schofer, N. Kaftzik, P. Wasserscheid, U. Kragl, Chem. Commun., 2001, 425. «Enzyme catalysis in ionic liquids: lipase catalysed kinetic resolution of 1-phenylethanol with improved enantioselecti vity «.
- J.H. Davis Jr, K.J. Forrester, Tetrahedron: Letters, 1999, 40, 1621. «Thiazolium-ion based ionic liquids (OILs). Novel OILs which promote the benzoin condensation».
- R. Breslow, J. Am. Chem. Soc. 1958, 80, 3719. «On the Mechanism of Thiamine Action. IV.1 Evidence from Studies on Model Systems».
- S. Toma, M. Meciarova, R, Sebesta, Eur.J.Org.Chem., 2009, 3, 321. «Are ionic liquids suitable media for organocatalytic reactions».
- P. Kotrusz, I. Kmentova, B. Gotov, S. Toma, E. Solcaniova, Chem Commun, 2002, 8, 2510. «Proline-catalysed asymmetric aldol reaction in the room temperature ionic liquid bmim. PF6».
- F.-F. Yong, C.-Y. Poh, G.-L. Chua, Y.-C. Teo, Chem.Lett., 2010, 39, 490. «Organocatalytic asymmetric syn-selective direct aldol reaction in ionic liquid».
- N.S. Chowdari, D.B. Ramachary, C.F.Barbas III, Synlett, 2003, 1906. «Organocatalysis in Ionic Liquids: Highly Efficient Z-Proline-Catalyzcd Direct Asymmetric Mannich Reactions Involving Ketone and Aldehyde Nucleophiles».
- P. Kortusz, S. Alemayehu, S. Toma, H.G. Schmalz, A. Alder, Eur. J. Org. Chem., 2005, 4904. «Enantioselective Organocatalysis in Ionic Liquids: Addition of Aliphatic Aldehydes and Ketones to Diethyl Azodicarboxylate».
- N. Kumaragurubaran, K. Juhl, W. Zhuang, A. Bogevig, K. A. Jorgensen, J. Am. Chem Soc, 2002,124, 6254. «Direct L-Proline-Catalyzed Asymmetric a-Animation of Ketones».
- D.-Q. Xu, B.-T. Wang, S.-P. Luo, H.-D. Yue, L.-P. Wang, Z.-Y. Xu, Tetrahedron: Asymmetry, 2007, 18, 1788. «Pyrrolidine-pyridinium based organocatalysts for highly enantioselective Michael addition of cyclohexanone to nitroalkenes».
- Park, B. Y.- Ryu, K. Y.- Park, J. H.- Lee, S.-g. Green Chem. 2009, 11, 946. «A, Dream Combination for Catalysis: Highly Reactive and Recyclable Scandium (III) Triflate-Catalyzed Cyanosilylations of Carbonyl Compounds in an Ionic Liquid».
- Oh, C. R.- Choo, D. J.- Shim, W. H.- Lee, D. H.- Roh, E. J.- Lee, S.-g.- Song, C. E. Chem. Commun. 2003, 1100. «Chiral Co (III)(Salen)-Catalysed Hydrolytic Kinetic Resolution of Racemic Epoxides in Ionic Liquids».
- J. Sirieix, Oflberger M., Betzemeier B., Knochel P., Synlett, 2000, 1613. «Palladium Catalyzed Cross-Couplings of Organozincs in Ionic Liquids».
- Y. Chauvin, L. Mussmann, H. Olivier. Angew. Chem. Int. Ed., 1996, 34, 23, 2698. «A Novel Class of Versatile Solvents for Two-Phase Catalysis: Hydrogenation, Isomerization, and
- Hydroformylation of Alkenes Catalyzed by Rhodium Complexes in Liquid 1,3-Dialkylimidazolium Salts».
- A.J. Carmichael, D.M. Haddleton, S.A.F. Bon, K.R. Seddon., Chem. Commun, 2000, 1237. «Copper (I) mediated living radical polymerisation in an ionic liquid».
- J. Dupont, R.F. de Souza, P.A.Z. Suarez, Chem. Rev. 2002, 102, 3667. «Ionic Liquid (Molten Salt) Phase Organometallic Catalysis».
- L. Xu, W. Chen, J. Xiao, Organometallies, 2000, 19, 1123. «Heck Reaction in Ionic Liquids and the in Situ Identification of iV-Heterocyclic Carbene Complexes of Palladium».
- S.-g. Lee, Chem. Commun., 2006, 1049. «Functionalized imidazolium salts for task-specific ionic liquids and their applications».
- P. J. Dyson, T.J. Geldbach, Electrochem. Soc Interface, Spring 2007 «Applications of Ionic Liquids in Synthesis and Catalysis»
- A.K. Chakraborti, S. Raha Roy, J. Am. Chem. Soc., 2009, 131, 6902. «On Catalysis by Ionic Liquids».
- D. Gu, S. Ji, II. Wang, Q. Xu, Synthetic Communications, 2008, 38: 8, 1212. «Acidic Ionic Liquid-Catalyzed Highly Efficient Reaction of Indoles to a, p-Unsaturated Ketones»
- B. C. Ranu, A. Saha, S. Banerjee, Eur. J. Org. Chem. 2008, 519. «Catalysis by Ionic Liquids: Significant Rate Acceleration with the Use of pmlmJBr in the Three-Component Synthesis of Dithiocarbamates».
- S. Luo, X. Mi, L. Zhang, S. Liu, H. Xu and J.-P. Cheng, Tetrahedron, 2007, 63, 1923. «Functionalized ionic liquids catalyzed direct aldol reactions».
- D. Xu, S. Luo, H. Yue, L. Wang, Y. Liu and Z. Xu, Synlett, 2006, 2569. «Ion-Supported Chiral Pyrrolidines as Enantioselective Catalysts for Direct Michael Addition of Nitroalkenes in BMIm. PF6>>
- S.G. Zlotin, N.N. Makhova, Mendeleev Commun., 2010, 20, 63. «Ionic liquids as substrate-specific recoverable solvents and catalysts of regio-, stereo- and enantioselective organic reactions»
- J.P. Brand, J.I.O. Siles, J. Waser, Synlett, 2010, 6, 0881. «Synthesis of chiral bifunctional (thio)urea N-heterocyclic carbenes».
- A.D. Hesdley, B. Ni. Aldrichimica Acta, 2007, 40,4, 107. «Chiral imidazolium ionic liquids: their synthesis and influence on the outcome of organic reactions».
- B. Gadenne, P. Hesemann, J. l J.E. Moreau, Tetrahedron: Asymmetry, 2005, 16, 2001. «Easily recoverable BINOL ligand with ionic tag for asymmetric catalysis».
- X. Feng, B. Pugin, E. K. usters, G. Sedelmeier, H.-U. Blaser, Adv.Synth. Catal., 2007, 349, 1803. «Josiphos Ligands with an Imidazolium Tag and their Application for the Enantioselective Hydrogenation in Ionic Liquids».
- W. Zhang, Y. Chi, X. Zhang, Acc. Chem. Res. 2007, 40, 1278. «Developing Chiral Ligands for Asymmetric Hydrogenation».
- Y. Peng, Y. Cai, G. Song, J. Chen, Synlett, 2005, 2147. «Ionic Liquid-Grafted Mn (III)-Schiff Base Complex: A Highly Efficient and Recyclable Catalyst for the Epoxidation of Chalcones».
- C. S. Consorti, G. L. P. Aydos, G. Ebeling, J. Dupont, Org. Lett., 2008, 10, 237. «Ionophilic Phosphines: Versatile Ligands for Ionic Liquid Biphasic Catalysis».
- A.M. Magill, K.J. Cavell, B.F. Yates, J. Am. Chem. Soc., 2004, 126, 8717. «Basicity of Nucleophilic Carbenes in Aqueous and Nonaqueous SolventssTheoretical Predictions».
- T.L. Amyes, S.T. Diver, J.P. Richard, F.M. Rivas, K. Toth.. Am. Chem. Soc., 2004, 126, 4366. «Formation and Stability of N-Heterocyclic Carbenes in Water: The Carbon Acid pKa of Imidazolium Cations in Aqueous Solution».
- Y. Chu, H. Deng, J.-P. Cheng, J. Org. Chem., 2007, 72, 7790. «An Acidity Scale of 1,3-Dialkylimidazolium Salts in Dimethyl Sulfoxide Solution».
- F.E. Hahn, M.C. Janke, Angew. Chem. Int. Ed., 2008, 47, 3122. «Heterocyclic crbenes: synthesis and coordination chemistry».
- D. Enders, A.A. Narine, J. Org. Chem., 2008, 73, 7857, «Lessons from Nature: Biomimetic Organocatalytic Carbon-Carbon Bond Formations».
- E. Peris, Top Organomet Chem., 2007, 21, S3. «Routes to N-Heterocyclic Carbene Complexes».
- H. M. J. Wang, I. J. B. Lin., Organometallics, 1998, 17, 972. «Facile Synthesis of Silver (I)-Carbene Complexes. Useful Carbene Transfer Agents».
- E. Colacino, J. Martinez, F. Lamaty. Coord. Chem. Rev., 2007, 251, 726. «Preparation of NHC-ruthenium complexes and their catalytic activity in metathesis reaction».
- N. Marion, S. P. Nolan. Acc. Chem. Res., 2008, 41, 11, 1440. «Well-Defined N-Heterocyclic Carbenes-Palladium (II) Precatalysts for Cross- Coupling Reactions».
- E. A. B. Kantchev, C. J. O’Brien, M. G. Organ., Angew. Chem. Int. Ed., 2007, 46, 2768. «Palladium Complexes of N-Heterocyclic Carbenes as Catalysts for Cross-Coupling Reactions—A Synthetic Chemist’s Perspective».
- F. Boeda, S.P. Nolan, Annu. Rep. Prog. Chem., Sect. B, 2008, 104, 184. «N-Heterocyclic carbene-containing complexes in catalysis».
- L. H. Gade, V. Cesar, S. Bellemin-Laponnaz, Angew. Chem.< Int. Ed., 2004- 43, 1014. «A Modular Assembly of Chiral Oxazolinylcarbene-Rhodium Complexes: Efficient Phosphane-Free Catalysts for the Asymmetric Hydrosilylation of Dialkyl Ketones».
- C. L. Winn, F. Guillen, J. Pytkowicz, S. Roland, P. Mangeney, A. Alexakis, J. Organomet. Chem. 2005, 690, 5672. «Enantioselective copper catalysed 1,4-conjugate addition reactions using chiral N-heterocyclic carbenes».
- J. Louie, J. E. Gibby, M. V. Farnworth, T. N. Tekavec, J. Am. Chem. Soc., 2002,124, 51,. 15 188. «Efficient Nickel-Catalyzed 2 + 2 + 2. Cycloaddition of CO2 and Diynes».
- J. C. Y. Lin, R. T. W. Huang- C. S. Lee, A. Bhattacharyya, W. S. Hwang, I. J. B. Lin, Chem. Rev., 2009- 109, 8, 3561. «Coinage Metal-N-Heterocyclic Carbene Complexes».
- L. Ricard, F. Gagosz, Organometallics, 2007, 26, 4704. «Synthesis and Reactivity of Air-Stable N-Heterocyclic Carbene Gold (I) Bis (trifluoromethanesulfonyl)imidate Complexes».
- D. Brissy, M. Skander, P. Retailleau, A. Marinetti. Organometallics, 2007, 26, 5782. «N-Heterocyclic Carbenes in the Synthesis of Axially Chiral Square-Planar Platinum Complexes».
- M. M. Rogers, S. S. Stahl, Top Organomet. Chem., 2007, 27, 21. «N-Heterocyclic Carbenes as Ligands for High-Oxidation-State Metal Complexes and Oxidation Catalysis».
- J. A. Mata, M. Poyatos, E. Peris, Coord. Chem. Rev., 2007, 251, 841. «Structural and catalytic properties of chelating bis- andtris-iV-heterocyclic carbenes».
- U. J. Scheele, S. D. Franc, Inorg. Chim. Acta, 2006, 359, 4891. «MeyerBridged dinucleating N-heterocyclic carbene ligands and their double helical mercury (II) complexes».
- G. Anantharaman, K. Elango, Organometallics, 2007, 26, 1089. «Synthesis and Characterization of NHC-Stabilized Zinc Aryloxide and Zinc Hydroxyaryloxide».
- P. L. Arnold, M. Rodden, K. M. Davis, A. C. Scarisbrick, A. J. Blake, C. Wilson, Chem. Commiin, 2004, 1612. «Asymmetric lithium (I) and copper (II) alkoxy-iV-heterocyclic carbene complexes- crystallographic characterisation and Lewis acid catalysis».
- P. L. Arnold, I. J. Casely, Chem. Rev., 2009, 109, 8, 3599. «F-Block N-IIeterocyclic Carbene Complexes».
- C. Najera, J. M. Sansano, Chem. Rev., 2007, 107, 4584. «Catalytic Asymmetric Synthesis of r-Amino Acids».
- C. Cativiela, M.D. Diaz-de-Villegas, Tetrahedron• Asymmetry, 1998, 9, 3517. «Stereoselective synthesis of quaternary a-amino acids. Part 1: Acyclic compounds».
- R.O. Duthaler, Tetrahedron, 1994, 6, 1539. «Recent developments in the stereoselective synthesis of a-aminoacids».
- T Abellan, T. Chinchilla, N. Galindo, G. Guillena, C. Najera, J. M. Sansano. Eur. J Org. Chem, 2000, 2689−2697. «Glycine and Alanine Imines as Templates for Asymmetric Synthesis of ct-Amino Acids».
- A. Hammershoi, A.M. Sargeson, W.L. Steffen. J. Am. Chem. Soc, 1984, 106, 10, 2819. «Reactivity studies of chelated maleate ion: stereoselectivity and structural correlations».
- R. G. Asperger, C. Fan. Inorg. Chem., 1967, 6, 4, 796. «LiuAsymmetric synthesis of alanine via the template action of a dissymmetric cobalt (III) complex».
- U. Schollkopf. Pure Appl. Chem., 1983,11, 1799−1806. «Asymmetric syntheses of amino acids via metalated bis-lactim ethers of 2,5-diketopiperazines».
- T. Qeulshausen- U. Groth- U. Schollkopf. Liebigs Ann. Chem. 1991, 1207−1209. «Asymmetric Syntheses via Heterocyclic Intermediates, XLV. Asymmetric Synthesis of Diastereomerically and Enantiomerically Pure 3-Substituted (2i?, 3iS)-serine Methyl Esters».
- W. Oppolzer- Ph Lienard. Helv. Chim. Acta. 1992, 75, 2572−2582. «Non-destructive Cleavage of iV-Acylsultams Under Neutral Conditions: Preparation of Enantiomerically, Pure Fmoc-Protected a -Amino Acids».
- W. Oppolzer, R, Moretti, S Thomi, Tetrahedron Lett, 1989, 30, 6009. «Asymmetric alkylations of a sultam-derived glycinate equivalent: practical preparation of enantiomerically pure a-amino acids».
- H. Josein, G. Chassaing, Tetrahedron: Asymmetry, 1992, 3, 1351. «Asymmetric synthesis of the diastereoisomers of L-l-indanylglycine and L-l-benzf.indanylglycine, %i, Xr cons trained side-chain derivatives of L-phenylalanine and L-2-naphthylalanine».
- S. Kanemasa, O. Uchida, E. Wada, J. Org. Chem. 1990, 55, 4411−4417. «Stereoselective Michael addition of the imines of a-amino esters in the presence of lithium, bromide/1,8-diazabicyclo5.4.0.undec-7-ene».
- J.M. Mcintosh, R.K. Leavitt, P. Mishra, K.C. Cassidy, J.E. Drake, R. Chadha. J. Org. Chem. 1988, 53, 1947−1952. «Diastereoselective alkylation guided by electrophile-nucleophile .pi.-interactions».
- Y.-Z: Jiang, C. Zhou, H. Piao. Synth. Commun. 1989,19, 881−888. «Asymmetric Synthesis. VII. Double Stereodifferentiation in Allylation of Ketimines Bearing Two Chiral Auxiliaries. Application to Enantioselective Synthesis of a-Allylglycine».
- S. Kanemasa, A. Tatsukawa, E. Wada. Chem. Lett. 1989, 1301−1304. «Absolutely Diastereoselective Asymmetric Michael Addition of the Camphor Imine of /-Butyl Aminoacetate with 2-Alkylidenemalonates».
- A. Solladie-Cavallo, М.С. Simon, Tetrahedron Lett, 1989, 30, 6011. «Enantioselective synthesis of optically pure natural S (+) or unnatural R (-) DABA».
- A.M. Panini, E. Nardi, F. Nuti, J. Uziel, M. Gianneschi, M. Chelli, A. Brandi. Eur. J. Org. Chern. 2002, 2736−2741. «Diastereoselective Alkylation of Schiff Bases for the Synthesis of Lipidic Unnatural Fmoc-Protected a.-Amino Acids».
- D. Seebach, M. Boes, R. Naef, W.B. Schweizer. J. Am. Chem. Soc. 1983, 105, 5390−5398. «Alkylation of amino acids without loss of the optical activity: preparation of.alpha.-substituted proline derivatives. A case of self-reproduction of chirality».
- M. Gander-Coquoz, D. Seebach. Helv. Chem. Acta, 1988, 71, 224−236. «Herstellung enantiomerenreiner, a-alkylierter Lysin-, Ornithin- und Tryptophan-Derivate».
- L. Zhang, J.M. Finn. J. Org. Chem., 1995, 60, 5719−5720. «А Facile Method for the Asymmetric Synthesis of.alpha.-Methyltryptophan».
- H8. R'.N. Krasikova, O. S: Fedorova, l.K. Mosevich, O.F. Kuznetsova, M.Y. Korsarov, S.M. Ametamey, P.A. Schubiger. J. Label Compds. Radiopharm. 1999, 42, SI02.
- St. Louis. J. Labelled Compd. Radiopharm. 1999, 42, 138.
- Y. Belokon. Janssen. Chim. Acta, 1992, 10, 2, 4. «(S)-2-N-(N'-benzylprolyl)amino.-benzophenone (BPB) a reagent for the synthesis of optically pure a-amino acids».
- Belokon', Y.N., Sagyan, A.S., Djamgaryan, S.M., Bakhmutov, V.I., Belikov, V.M. Tetrahedron, 1988, 44, 5507. «Asymmetric synthesis of p-substituted a-amino acids via a chiral Ni» complex of dehydroalanine».
- G. V. S. M. Carrera, С. A. M. Afonso, L. C. Branco, J. Chem. Eng. Data 2010, 55, 609. «Interfacial Properties, Densities, and Contact Angles of Task Specific Ionic Liquids».
- H.-C. Ma, X.-Z. Jiang, J.Org. Chem., 2007, 72, 8943. «N-Hydroxyimides as efficient ligands for the copper-catalyzed N-arylation of pyrrole, imidazole and indole».
- Q.-A. Chen, D.-S. Wang, Y.-G. Zhou, Chem. Commun., 2010, 46, 4043. «Bifunctional AgOAc-catalyzed asymmetric reactions».
- S. Mukherjee, J.W. Yang, S. Hoffmann, B. List, Chem. Rev., 2007, 107, 12, 5471. «Asymmetric Enamine Catalysis».
- Т. Капо, K. Sasaki, T. Konishi, H. Mii, K. Maruoka, Tetrahedron Letters, 2006, 47, 4615. «Highly efficient trialkylsilylcyanation of aldehydes, ketones and imines catalyzed by a nucleophilic N-heterocyclic carbene».
- J.J. Song, F. Gallou, J. T. Reeves, Z. Tan, N. K. Yee, С. H. Senanayake, J. Org. Chem., 2006, 71, 3, 1273. «Activation of TMSCN by N-I leterocyclic Carbenes for Facile Cyanosilylation of Carbonyl Compounds».
- Y. Suzuki, Abu Bakar M.D., K. Muramatsu, M. Sato, Tetrahedron, 2006, 62, 4227. «Cyanosilylation of aldehydes catalyzed by iV-heterocyclic carbenes». 134 http://www.chem.wise.edu/areas/reich/pkatable/
- J.-A. Ma, D. Cahard, Chem. Rev., 2004, 104, 6119. «Asymmetric Fluorination, Trifluoromethylation, and Perfluoroalkylation Reactions».
- T. Billard, B. R. Langlois, Eur. J. Org. Chem., 2007, 891. «How to Reach Stereogenic Trifluoromethylated Carbon? En Route to the «Grail» of the Asymmetric Trifluoromethylation Reaction».
- Гордон А., Форд P., «Спутник химика» M.: Мир, 1976, 437.
- G.M.Sheldrick, SADABS, v. 2.03, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA, 2003.
- A.L.Spek. PLATON, A Multipurpose Crystallographic Tool, Utrecht University, The Netherlands, 1998.
- G.M.Sheldrick, Acta Cryst., 2008, A64, 112−122. «A short history of SHELX»
- Frederic Guillen, Delphine Bregeon and Jean-Christophe Plaquevcnt, Tetrahedron Letters, 2006, 47, 1245. «fiS^-Histidine: the ideal precursor for a novel family of chiral aminoacid and peptidic ionic liquids».