Синтез новых биядерных хиральных катализаторов и их использование в асимметрическом образовании связи углерод-углерод тема диссертации и автореферата по ВАК РФ 02.00.03, кандидат химических наук Чусов, Денис Александрович

• Чусов, Денис Александрович
• кандидат химических наук
• 2008

Оглавление диссертации кандидат химических наук Чусов, Денис Александрович

Оглавление

Список используемых сокращений

I. Введение 4 И. Литературный обзор

II. 1. Сравнение биядерного и моноядерного катализа 6 П. 1.1 Первые хиральные биядерные катализаторы 6 II. 1.2 Биядерный катализатор Троста (В.М. Trost) 8 II. 1.3 Биядерный кобальт-саленовый катализатор Джекобсена (E.N. Jacobsen) 14 II. 1.4 Биядерный хром-саленовый катализатор Джекобсена (E.N. Jacobsen) 17 II. 1.5 Биядерный алюминий-саленовый катализатор Джекобсена (E.N. Jacobsen) 20 II. 1.6 Биядерный титан-саленовый катализатор Белоконя (Y.N. Belokon) 28 II. 1.7 Биядерные ванадиевые катализаторы Гонга (L. Gong) 33 II. 2. Другие биядерные катализаторы 39 II. 3. Реакция асимметрического триметилсилилцианирования альдегидов 46 II. 4. Реакция асимметрического аллилирования альдегидов

II. 5. Реакции асимметрического раскрытия мезо-эпоксидов

III. Постановка задачи

IV. Обсуждение результатов 75 IV. 1. Синтез хиральных гексадентатных лигандов 75 IV. 2. Реакция асимметрического циансилилирования альдегидов 83 IV. 3. Реакция асимметрического аллилирования альдегидов

IV. 4. Реакция асимметрического раскрытия мезо-эпоксидов 100 триметилсилилцианидом

V. Выводы

VI. Экспериментальная часть

Список литературы диссертационного исследования кандидат химических наук Чусов, Денис Александрович, 2008 год

1. C. Gerdemann, C. Eicken, B. Krebs; Acc. Chem. Res., 2002, 35, 183. «The Crystal Structure of Catechol Oxidase: New Insight into the Function of Type-3 Copper Proteins».

2. B.J. Wallar, J.D. Lipscomb; Chem. Rev., 1996, 96, 2625. «Dioxygen Activation by Enzymes Containing Binuclear Non-Heme Iron Clusters».

3. Stenkamp R.E.; Chem. Rev. 1994, 94, 715. «Dioxygen and Hemerythrin».

4. Katsuki, Т.; Sharpless, К. B. J. Am. Chem. Soc. 1980, 102, 5974-5976. «The first practical method for asymmetric epoxidation».

5. Corey, E. J. J. Org. Chem. 1990, 55, 1693-1694. «On the origin of enantioselectivity in the Katsuki- Sharp less epoxidation procedure».

6. Woodard, S. S.; Finn, M. G.; Sharpless, К. B. J. Am. Chem. Soc. 1991, 113, 106-113. «Mechanism of asymmetric epoxidation. 1. Kinetics».

7. Finn, M. G.; Sharpless, К. B. J. Am. Chem. Soc. 1991,113, 113-126; «Mechanism of Asymmetric Epoxidation. 2. Catalyst Structure».

8. M. Kitamura, S. Suga, M. Niwa, R. Noyori, J. Am. Chem. Soc. 1995, 117, 4832 4842. «Self and Nonself Recognition of Asymmetric Catalysts. Nonlinear Effects in the Amino Alcohol-Promoted Enantioselective Addition of Dialkylzincs to Aldehydes»

9. M. Yamakawa, R. Noyori, J. Am. Chem. Soc. 1995,117, 6327 6335. «An Ab Initio Molecular Orbital Study on the Amino Alcohol-Promoted Reaction of Dialkylzincs and Aldehydes».

10. В . Goldfuss, K. N. Houk, J. Org. Chem. 1998, 63, 8998 9006. «Origin of Enantioselectivities in Chiral a-Amino Alcohol Catalyzed Asymmetric Additions of Organozinc Reagents to Benzaldehyde: PM3 Transition State Modeling».

11. M. Yamakawa, R. Noyori, Organometallics 1999, 18, 128 133. «Asymmetric Addition of Dimethylzinc to Benzaldehyde Catalyzed by (25)-3-exo-(Dimethylamino)isobornenol. A Theoretical Study on the Origin of Enantioselection».

12. В . Goldfuss, M. Steigelmann, S. I. Khan, K. N. Houk, J. Org. Chem. 2000, 65, 77 82. «Rationalization of Enantioselectivities in Dialkylzinc Additions to Benzaldehyde Catalyzed by Fenchone Derivatives».

13. L. Pu, H.-B. Yu, Chem. Rev. 2001,101, 757 824. «Catalytic Asymmetric Organozinc Additions to Carbonyl Compounds».

14. M. Panda, P.-W. Phuan, M. C. Kozlowski, J. Org. Chem. 2003, 68, 564 571. «Theoretical and Experimental Studies of Asymmetric Organozinc Additions to Benzaldehyde Catalyzed by Flexible and Constrained y-Amino Alcohols».

15. M. C. Kozlowski, S. L. Dixon, M. Panda, G. Lauri, J. Am. Chem. Soc. 2003,125, 6614 -6615. «Quantum Mechanical Models Correlating Structure with Selectivity: Predicting the Enantioselectivity of a-Amino Alcohol Catalysts in Aldehyde Alkylation».

16. Barry M. Trost, Hisanaka Ito, and Elliad R. Silcoff, J. Am. Chem. Soc. 2001, 123, 3367-3368. «Asymmetric Aldol Reaction via a Dinuclear Zinc Catalyst: a-Hydroxyketones as Donors».

17. Barry M. Trost, Vince S. C. Yeh, Hisanako Ito, and Nadine Bremeyer, Org. Lett., 2002, 4, 16, 2621-2623. «Effect of Ligand Structure on the Zinc-Catalyzed Henry Reaction. Asymmetric Syntheses of (-)-Denopamine and (-)-Arbutamine».

18. Barry M. Trost, Elliad R. Silcoff, and Hisanaka Ito, Org. Lett., 2001, 3, 16, 2497-2500. «Direct Asymmetric Aldol Reactions of Acetone Using Bimetallic Zinc Catalysts».

19. Barry M. Trost, Vince S. C. Yeh, Angew. Chem. Int. Ed. 2002, 41, 5, 861-863. «А Dinuclear Zn Catalyst for the Asymmetric Nitroaldol (Henry) Reaction».

20. Barry M. Trost, Christoph Muller, J. Am. Chem. Soc. 2008,130, 2438-2439. «Asymmetric Friedel-Crafts Alkylation of Pyrroles with Nitroalkenes Using a Dinuclear Zinc Catalyst».

21. Barry M. Trost, David W. Lupton, Org. Lett., 2007, 9, 10, 2023-2026. «Dinuclear Zinc-Catalyzed Enantioselective Aza-Henry Reaction».

22. D. Allen Annis and Eric N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 4147-4154. «Polymer-Supported Chiral Co(Salen) Complexes: Synthetic Applications and Mechanistic Investigations in the Hydro lytic Kinetic Resolution of Terminal Epoxides».

23. Rolf Breinbauer and Eric N. Jacobsen, Angew. Chem. Int. Ed., 2000, 39, 20, 3604-3607. «Cooperative Asymmetric Catalysis with Dendrimeric Co(salen). Complexes».

24. Joseph M. Ready and Eric N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687-2688. «Highly Active Oligomeric (salen)Co Catalysts for Asymmetric Epoxide Ring-Opening Reactions».

25. Joseph M. Ready and Eric N. Jacobsen, Angew. Chem. Int. Ed. 2002, 41, 8, 1374-1377. «А Practical Oligomeric (salen)Co. Catalyst for Asymmetric Epoxide Ring-Opening Reactions».

26. Thomas Belser and Eric N. Jacobsen, Adv. Synth. Catal. 2008, 350, 967 -971. «Cooperative Catalysis in the Hydrolytic Kinetic Resolution of Epoxides by Chiral (salen)Co (III). Complexes Immobilized on Gold Colloids».

27. Karl В. Hansen, James L. Leighton, and Eric N. Jacobsen, J. Am. Chem. Soc. 1996,118, 10924-10925. «On the Mechanism of Asymmetric Nucleophilic Ring-Opening of Epoxides Catalyzed by (Salen)Crlll Complexes».

28. Reed G. Konsler, Jorn Karl, and Eric N. Jacobsen, J. Am. Chem. Soc. 1998,120, 10780-10781. «Cooperative Asymmetric Catalysis with Dimeric Salen Complexes».

29. Glenn M. Sammis, Hiroshi Danjo, and Eric N. Jacobsen, J. Am. Chem. Soc. 2004,126, 99289929. «Cooperative Dual Catalysis: Application to the Highly EnantioselectiveConjugate Cyanation of Unsaturated Imides».

30. Clement Mazet and Eric N. Jacobsen, Angew. Chem. Int. Ed. 2008, 47, 1762 -1765. «Dinuclear {(salen)Al} Complexes Display Expanded Scope in the Conjugate Cyanation of a,b-Unsaturated Imides».

31. Mark Gandelman and Eric N. Jacobsen, Angew. Chem. Int. Ed. 2005, 44, 2393 -2397. «Highly Enantioselective Catalytic Conjugate Addition of N-Heterocycles to a,p-Unsaturated Ketones and Imides».

32. Mark S. Taylor, David N. Zalatan, Andreas M. Lerchner, and Eric N. Jacobsen, J. Am. Chem. Soc. 2005,127, 1313-1317. «Highly Enantioselective Conjugate Additions to a,P-Unsaturated Ketones Catalyzed by a (Salen)Al Complex».

33. Mark S. Taylor, Eric N. Jacobsen, J. Am. Chem. Soc. 2003,125, 11204-11205. «Enantioselective Michael Additions to a,P-Unsaturated Imides Catalyzed by a Salen-Al Complex».

34. Christopher D. Vanderwal and Eric N. Jacobsen, J. Am. Chem. Soc. 2004,126, 14724-14725. «Enantioselective Formal Hydration of a,p-Unsaturated Imides by Al-CatalyzedConjugate Addition of Oxime Nucleophiles».

35. Y. Belokon, N. Ikonnikov, M. Moscalenko,M. North, S. Orlova, V. Tararov, L. Yashkina, Tetrahedron : Asymmetry 1996, 7, 851 855. «Asymmetric trimethylsilylcyanation of aldehydes catalyzed by chiral (salen)Ti(IV) complexes».

36. Y. Belokon, M. Flego, N. S. Ikonnikov, M. Moscalenko, M. North, C. Orizu, V. Tararov, M. Tasinazzo, J. Chem. Soc. Perkin Trans. 1 1997, 1293 1295. «Asymmetric addition of trimethylsilyl cyanide to aldehydes catalysed by chiral (salen)TiIV complexes».

37. Yuri N. Belokon', A. John Blacker, Paola Carta, Lisa A. Clutterbuck and Michael North, Tetrahedron 2004, 60, 10433-10447. «Synthetic and mechanistic studies on asymmetric cyanohydrin synthesis using a titanium(salen) bimetallic catalyst».

38. N. Prabagaran and G. Sundararajan, Tetrahedron : Asymmetry 2002,13, 1053-1058. «Asymmetric Michael addition reactions using a chiral La-Na aminodiolate catalyst».

39. Ken-ichi Yamada, Simon J. Harwood, Harald Groger, and Masakatsu Shibasaki, Angew. Chem. Int. Ed. 1999, 38, 23, 3504-3506. «The First Catalytic Asymmetric Nitro-Mannich-Type Reaction Promoted by a New Heterobimetallic Complex».

40. Takayoshi Arai, Qiao-Sheng Hu, Xiao-Fan Zheng, Lin Pu, Hiroaki Sasai, Org. Lett. 2000, 2, 26, 4261-4263. «Immobilization of Heterobimetallic Multifunctional Asymmetric Catalyst».

41. Katsuya Matsui, Shinobu Takizawa and Hiroaki Sasai, Tetrahedron Letters 2005, 46, 19431946. «Enantioselective Morita-Baylis-Hillman (MBH) reaction promoted by a heterobimetallic complex with a Lewis base».

42. Hiroaki Sasai, Shigeru Arai, Yoshihiro Tahara, Masakatsu Shibasaki, J. Org. Chem. 1996, 60, 6656-6657. «Catalytic Asymmetric Synthesis of a-Amino Phosphonates Using Lanthanoid-Potassium-BINOL Complexes».

43. Tsuyoshi Mita, Kazuki Sasaki, Motomu Kanai and Masakatsu Shibasaki, J. Am. Chem. Soc. 2005,127, 514-515. «Catalytic Enantioselective Conjugate Addition of Cyanide to a,p-Unsaturated N-Acylpyrroles».

44. Yuta Tanaka, Motomu Kanai and Masakatsu Shibasaki, J. Am. Chem. Soc. 2008,130, 60726073. «А Catalytic Enantioselective Conjugate Addition of Cyanide to Enones».

45. Tsuyoshi Mita, Ikuo Fujimori, Reiko Wada, Jianfeng Wen, Motomu Kanai, and Masakatsu Shibasaki, J. Am. Chem. Soc. 2005,127, 11252-11253. «Catalytic Enantioselective Desymmetrization of meso-N-Acylaziridines with TMSCN».

46. Shinya Handa, Yijay Gnanadesikan, Shigeki Matsunaga, and Masakatsu Shibasaki, J. Am. Chem. Soc. 2007, 129, 4900-4901. «syn-Selective Catalytic Asymmetric Nitro-Mannich Reactions Using a Heterobimetallic Cu-Sm-Schiff Base Complex».

47. Rebecca T. Ruck and Eric N. Jacobsen, J. Am. Chem. Soc. 2002,124, 2882-2883. «Asymmetric Catalysis of Hetero-Ene Reactions with Tridentate Schiff Base Chromium(III) Complexes».

48. Karl Gademann, David E. Chavez, Eric N. Jacobsen, Angew. Chem. Int. Ed. 2002, 41, 16, 3059-3061. «Highly Enantioselective Inverse-Electron-Demand Hetero-Diels-Alder Reactions of a,P-Unsaturated Aldehydes».

49. Elizabeth R. Jarvo, Brian M. Lawrence, Eric N. Jacobsen, Angew. Chem. Int. Ed. 2005, 44, 6043 -6046. «Highly Enantio- and Regioselective Quinone Diels-Alder Reactions Catalyzed by a Tridentate (Schiff Base)CrIII. Complex».

50. Melissa L. Grachan, Matthew T. Tudge, and Eric. N. Jacobsen, Angew. Chem. Int. Ed. 2008, 47, 1469-1472. «Enantioselective Catalytic Carbonyl-Ene Cyclization Reactions».

51. Michael North, Tetrahedron : Asymmetry, 2003,14, 147—176. «Synthesis and applications of non-racemic cyanohydrins».

52. Jean-Michel Brunei, Ian P. Holmes, Angew. Chem. Int. Ed., 2004, 43, 2752 2778, «Chemically Catalyzed Asymmetric Cyanohydrin Syntheses»

53. Thierry R. J. Achard, Lisa A. Clutterbuck, Michael North, Synlett, 2005,12, 1828-1847, «Asymmetric Catalysis of Carbon-Carbon Bond-Forming Reactions Using Metal(salen) Complexes»

54. Noor-ul H. Khan, Rukhsana I. Kureshy, Syed H.R. Abdi, Santosh Agrawal, Raksh V. Jasra, Coordination Chemistry Reviews, 2008, 252, 593-623, «Metal catalyzed asymmetric cyanation reactions»

55. Scott E. Denmark, Jiping Fu; Chem. Rev. 2003,103, 2763-2793 «Catalytic Enantioselective Addition of Allylic Organometallic Reagents to Aldehydes and Ketones»

56. Yoshinori Yamamoto, Naoki Asao, Chem. Rev. 1993, 93, 2207-2293 «Selective Reactions Using Allylic Metals»

57. Angelo de Fatima, Luis Gustavo Robello e Ronaldo Aloise Pilli, Quim. Nova, 2006, 29, 5, 1009-1026, «ALILACAO E CROTILAQAO CATAL1TICA E ENANTIOSSELETIVA DE ALDEIDOS»

58. Hideo Hanawa, Satoshi Kii, Naoki Asao, Keiji Maruoka, Tetrahedron Letters, 2000, 41 5543-5546, «Bis-zirconium and bis-hafnium catalysts for the strong activation of carbonyl substrates»

59. Satoshi Kii, Keiji Maruoka; Tetrahedron Letters, 2001, 42, 1935-1939; «Practical approach for catalytic asymmetric allylation of aldehydes with a chiral bidentate titanium(IV) complex»

60. William R. Roush, Jennifer A. Champoux and Barry C. Peterson, Tetrahedron Letters, 1996, 37, 50, 8989-8992. «Diastereoselective Synthesis of the Cis.Octahydronaphthalene Nucleus of Superstolides A and В».

61. Gary E. Keck, Carrie A. Wager, Travis T. Wager, Kenneth A. Savin, Jonathan A. Covel, Mark D. McLaws, Dhileep Krishnamurthy, Victor J. Cee, Angew. Chem. Int. Ed. 2001, 40, 1, 231-234. «Asymmetric Total Synthesis ofRhizoxin D».

62. Hideo Hanawa, Takuya Hashimoto, Keiji Maruoka, J. Am. Chem. Soc., 2003,125, 17081709, <<Bis(((S)-bmaphthoxy)(isopropoxy)titanium) Oxide as a ju-Oxo-Type Chiral1.wis Acid: Application to Catalytic Asymmetric Allylation of Aldehydes».

63. Satoshi Kii, Keiji Maruoka, Chirality 2003,15, 68-70, «Catalytic Enantioselective Allylation of Ketones with Novel Chiral Bis-Titanium(IV) Catalyst»

64. Cole B.M., Shimizu K.D., Krueger C.A., Harrity J.P.A., Snapper M.L., Hoveyda A.H.; Angew. Chem. Int. Ed. 1996, 35, 15, 1668 «Discovery of Chiral Catalysts through Ligand Diversity : Ti-Catalyzed Enantioselective Addition of TMSCN to meso Epoxides»

65. Shimizu K.D., Cole B.M., Krueger C.A., Kuntz K.W., Snapper M.L., Hoveyda A.H.; Angew. Chem. Int. Ed. 1997, 36, 16, 1703. «Search for Chiral Catalysts Through Ligand Diversity: Substrate-Specific Catalysts and Ligand Screening on Solid Phase»

66. Schaus S.E., JacobsenE.N.; Org. Lett. 2000, 2,7, 1001. «Asymmetric Ring Opening of Meso Epoxides with TMSCN Catalyzed by (pybox)lanthanide Complexes».

67. Vougioukas, A. E.; Kagan, H. B. Tetrahedron Lett. 1987, 28, 5513. «Lanthanides as lewis-acid catalysts in aldol addition,cyanohydrin-forming and oxirane ring opening reactions».

68. Matsubara, S.; Onishi, H.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6209-6212. «Reaction of cyanotrimethylsilane with oxiranes under Yb(CN)3 catalysis»

69. Saha В., Lin M.-H., RajanBabu T.V.; J. Org. Chem. 2007, 72, 8648. «Exceptionally Active Yttrium-Salen Complexes for the Catalyzed Ring Opening of Epoxides by TMSCN and TMSN3»

70. Jacobsen, E. Acc. Chem. Res. 2000, 33, 421. «Asymmetric Catalysis of Epoxide Ring-Opening Reactions».

71. Chengjian Zhu, Fang Yuan, Weijin Gu, Yi Pan, Chem. Comm., 2003, 692-693. «The first example of enantioselective isocyanosilylation of meso epoxides with TMSCN catalyzed by novel chiral organogallium and indium complexes».

72. K. Imi, N. Yanagihara, K. Utimoto, J. Org. Chem., 1987, 52, 1013-1016. «Reaction of Cyanotrimethylsilane with Oxiranes. Effects of Catalysts or Mediators on Regioselectivity and Ambident Character».

73. Keisuke Sugita, Akihisa Ohta, Makoto Onaka, Yusuke Izume, Chem. Lett., 1990, 481-484. «Solid Base-directed Regioselective Ring Opening of Epoxides with Cyanotrimethylsilane».

74. B. Sharpless, J. Org. Chem., 1985, 50, 9, 1557-1560. «Ti(0-i-Pr)4-Mediated Nucleophilic Openings of 2,3-Epoxy Alcohols. A Mild Procedure for Regioselective Ring-Opening».

75. Hiroyuki Konno, Emi Toshiro, Naoyuki Hinoda, Synthesis 2003, 14, 2161-2164. «An Epoxide Ring-Opening Reaction via Hypervalent Silicate Intermediate: Synthesis of Statine».

76. Do Hyun Ryu, E. J. Corey, J. Am. Chem. Soc., 2005,127, 5384-5387. «Enantioselective Cyanosilylation of Ketones Catalyzed by a Chiral Oxazaborolidinium Ion».

77. M. S. Sigman; P. Vachal; E. N. Jacobsen, Angew. Chem. Int. Ed. 2000, 39, 1279-1281. «А General Catalyst for the Asymmetric Strecker Reaction»

78. F. G. Glansdorp, G. L. Thomas, J. K. Lee, J. M. Dutton, G. P. C. Salmond, M. Welch, D. R. Spring, Org. Biomol. Chem., 2004, 2, 3329. «Synthesis and stability of small molecule probes for Pseudomonas aeruginosa quorum sensing modulation».

79. H.-C. Zhang, W.-S. Huang, L. Pu, J. Org. Chem., 2001, 66, 481-487. «Biaryl-Based Macrocyclic and Polymeric Chiral (Salophen)Ni(II) Complexes: Synthesis and Spectroscopic Study».

80. M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc., 1997,119, 2329. «Catalytic Asymmetric Epoxidation of a,P-Unsaturated Ketones Promoted by Lanthanoid Complexes».

81. D.A. Evans, M.D. Ennis, DJ. Mathre, J. Am. Chem. Soc., 1982,104, 1737. «Asymmetric alkylation reactions of chiral imide enolates. A practical approach to the enantioselective synthesis of .alpha.-substituted carboxylic acid derivatives».

82. M.J. McKennon, A.I. Meyers, K. Drauz, M. Schwarm, J. Org. Chem., 1993, 58, 3568. «А convenient reduction of amino acids and their derivatives».

83. Meyers A.I., Knaus G., Kamata K, Ford M.E., J. Am. Chem. Soc., 1976, 98, 2, 567. «Asymmetric synthesis of R and S .alpha.-alkylalkanoic acids from metalation and alkylation of chiral 2-oxazolines».

84. T. Mecca, S. Superchi, G. Egidio, C. Rosini, Tetrahedron : Asymmetry, 2001,12, 1225. «1,1'-Binaphthylazepine-based ligands for asymmetric catalysis. Part 1: Preparation and characterization of some new aminoalcohols and diamines».

85. Hayashi, M.; Miyamoto, Y.; Inoue, Т.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522. «Enantioselective trimethylsilylcyanation of some aldehydes catalyzed by chiral Schiff base-titanium alkoxide complexes».

86. M. T. Reetz; P. Kunisch; P. Heitmann, Tetrahedron Lett. 1986, 27, 4721. «Chiral Lewis acids for enantioselective C-C bond formation».

87. J. Brussee, E.C. Roos, A. Van der Gen, Tetrahedron Lett., 1988, 29, 4485-4488 «Bio-organic synthesis of optically active cyanohydrins and acyloins».

88. Brown, H. C.; Jadhav, P. K. J. Org. Chem. 1984, 49, 4089. «В-Allyldiisocaranylborane: a new, remarkable enantioselective allylborating agent for prochiral aldehydes. Synthesis of homoallylic alcohols approaching 100% enantiomeric purities».

89. G.M. Sheldrick, SHELXTL Plus, PC Version, a. System of Computer Programs for the Determination of Crystal Structure from X-ray Diffraction Data, Rev. 502, Siemens Analytical X-Ray Instruments Inc., Germany, 1994.