Power of cooperativity: Lewis acid-Lewis base bifunctional asymmetric catalysis

Synlett

Volumn , Issue 10, 2005, Pages 1491-1508

  Kanai, Motomu ^a,b   Kato, Nobuki ^b   Ichikawa, Eiko ^b   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Asymmetric synthesis; Catalysis; Imines; Lewis acids; Pyridines

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; ALDEHYDE; BASE; IMINE; ISOQUINOLINE; KETONE; LEWIS ACID; PYRIDINE DERIVATIVE; QUINOLINE;

ASYMMETRIC CATALYSIS; COOPERATION; ENANTIOSELECTIVITY; ENERGY RESOURCE; REVIEW; SILYLATION;

EID: 21544444468     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-869831     Document Type: Review

References (89)

1. (a) Ma, J.-A.; Cahard, D. Angew. Chem. Int. Ed. 2004, 43, 4566.
2. (b) Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989.
3. (c) Shibasaki, M.; Kanai, M. Chem. Pharm. Bull. 2001, 49, 511.
4. (d) Rawlands, G. J. Tetrahedron 2001, 57, 1865.
5. (e) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1991, 36, 1236.
6. Review: Machajewski, T. D.; Wong, C.-H. Angew. Chem. Int. Ed. 2000, 39, 1352.
7. (a) Evans, D. A.; Truesdale, L. K.; Carroll, G. L. J. Chem. Soc., Chem. Commun. 1973, 55.
8. (b) Lidy, W.; Sundermeyer, W. Chem. Ber. 1973, 106, 587.
9. (a) Evans, D. A.; Wong, R. Y. J. Org. Chem. 1977, 42, 350.
10. (b) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537.
11. For a recent review, see: Brunel, J.-M.; Holmes, I. P. Angew. Chem. Int. Ed. 2004, 43, 2752.
12. For examples of bifunctional catalysts in enantioselective cyanosilylation of aldehydes, see: (a) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 541.
13. (b) Casas, J.; Nájera, C.; Sansano, J. M.; Saá, J. M. Org. Lett. 2002, 4, 2589.
14. (c) Rowlands, G. J. Synlett 2003, 236.
15. (d) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8106.
16. Corey, E. J.; Helal, C. J. Angew. Chem. Int. Ed. 1998, 37, 1986.
17. Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
18. (a) Hamashima, Y.; Sawada, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 2641.
19. (b) Hamashima, Y.; Sawada, D.; Nogami, H.; Kanai, M.; Shibasaki, M. Tetrahedron 2001, 57, 805.
20. For other examples of beneficial effects of a proton source in catalytic enantioselective reactions, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedow, J. S. J. Am. Chem. Soc. 1999, 121, 1994.
21. (b) Josephsohn, N. S.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 11594.
22. (c) Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292; see also ref. 14.
23. (a) Takamura, M.; Yanagisawa, H.; Kanai, M.; Shibasaki, M. Chem. Pharm. Bull. 2002, 50, 1118.
24. (b) Nogami, H.; Kanai, M.; Shibasaki, M. Chem. Pharm. Bull. 2003, 51, 702.
25. Sawada, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 10521.
26. For the observation of the isomerization of silyl nitriles to silyl isonitriles by IR, see: Seckar, J. A.; Thayer, J. S. Inorg. Chem. 1976, 15, 501.
27. (a) Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem. Int. Ed. 2000, 39, 1650.
28. (b) Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Chem. Pharm. Bull. 2000, 48, 1586.
29. Nogami, H.; Matsunaga, S.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 279.
30. For reviews, see: (a) Popp, F. D. Heterocycles 1973, 1, 165.
31. (b) McEwen, W. E.; Cobb, R. L. Chem. Rev. 1955, 55, 511.
32. (a) Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6327.
33. (b) Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 6801.
34. Leeson, P. D.; Carling, R. W.; Moore, K. W.; Moseley, A. M.; Smith, J. D.; Stevenson, G.; Chan, T.; Baker, R.; Foster, A. C.; Grimwood, S.; Kemp, J. A.; Marshall, G. R.; Hoogsteen, K. J. Med. Chem. 1992, 35, 1954.
35. Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784.
36. For recent reviews, see: (a) Buffat, M. G. P. Tetrahedron 2004, 60, 1701.
37. (b) Laschat, S.; Dickner, T. Synthesis 2000, 1781.
38. For selected examples, see: (a) Comins, D. L.; Goehring, R. R.; Joseph, S. P.; O'Connor, S. J. Org. Chem. 1990, 55, 2574.
39. (b) Gosmini, R.; Mangeney, P.; Alexakis, A.; Commerçon, M.; Normant, J.-F. Synlett 1991, 111.
40. (c) Génisson, Y.; Marazano, C.; Das, B. C. J. Org. Chem. 1993, 58, 2052.
41. (d) Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829.
42. (e) Yamada, S.; Morita, C. J. Am. Chem. Soc. 2002, 124, 8184.
43. (f) Legault, C.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 6360.
44. Reuss, R. H.; Smith, N. G.; Winters, L. J. J. Org. Chem. 1974, 39, 2027.
45. Popp, F. D.; Takeuchi, I.; Kant, J.; Hamada, Y. J. Chem. Soc., Chem. Commun. 1987, 1765.
46. Ichikawa, E.; Suzuki, M.; Yabu, K.; Albert, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 11808.
47. Sanner, M. A.; Chappie, T. A.; Dunaiskis, A. R.; Fliri, A. F.; Desai, K. A.; Zorn, S. H.; Jackson, E. R.; Johnson, C. G.; Morrone, J. M.; Seymour, P. A.; Majchrzak, M. J.; Faraci, W. S.; Collins, J. L.; Duignan, D. B.; Di Prete, C. C.; Lee, J. S.; Trozzi, A. Bioorg. Med. Chem. Lett. 1998, 8, 725.
48. For recent examples of advances in this field, see: (a) Dosa, P. I.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 445.
49. (b) Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233.
50. (c) Jeon, S.-J.; Walsh, P. J. J. Am. Chem. Soc. 2003, 125, 9544.
51. (d) Ramon, D. J.; Yus, M. Tetrahedron Lett. 1998, 54, 5651.
52. (e) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536.
53. (f) Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910.
54. (g) Suto, Y.; Kumagai, N.; Matsunaga, S.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 3147.
55. (h) Oisaki, K.; Suto, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5644.
56. For example, see: Kiljunen, E.; Kanerva, L. T. Tetrahedron: Asymmetry 1997, 8, 1151.
57. Kanai, M.; Hamashima, Y.; Shibasaki, M. Tetrahedron Lett. 2000, 41, 2405.
58. Hamashima, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 7412.
59. For examples of catalytic enantioselective cyanation of ketones from other groups, see: (a) Belokon', Y. N.; Green, B.; Ikonnikov, N. S.; North, M.; Tararov, V. I. Tetrahedron Lett. 1999, 38, 6669.
60. (b) Belokon', Y. N.; Caveda-Cepas, S.; Green, B.; Ikonnikov, N. S.; Khrustalev, V. N.; Larichev, V. S.; Moscalenko, M. A.; North, M.; Orizu, C.; Tararov, V. I.; Tasinazzo, M.; Timofeeva, G. I.; Yashkina, L. V. J. Am. Chem. Soc. 1999, 121, 3968.
61. (c) Belokon', Y. N.; Green, B.; Ikonnikov, N. S.; Larichev, V. S.; Lokshin, B. V.; Moscalenko, M. A.; North, M.; Orizu, C.; Peregudov, A. S.; Timofeeva, G. I. Eur. J. Org. Chem. 2000, 2655.
62. (d) Belokon', Y. N.; Green, B.; Ikonnikov, N. S.; North, M.; Parsons, T.; Tararov, V. I. Tetrahedron 2001, 57, 771.
63. (e) Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2001, 123, 6195.
64. (f) Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2003, 125, 9900.
65. (g) Deng, H.; Isler, M. P.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem. Int. Ed. 2002, 41, 1009.
66. (h) Chen, F.; Feng, Z.; Qin, B.; Zhang, G.; Jiang, Y. Org. Lett. 2003, 5, 949.
67. (i) Shen, Y.; Feng, X.; Li, Y.; Zhang, G.; Jiang, Y. Eur. J. Org. Chem. 2004, 129.
68. Yabu, K.; Masumoto, S.; Yamasaki, S.; Hamashima, Y.; Kanai, M.; Du, W.; Curran, D. P.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 9908.
69. Fujii, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733.
70. Takamura, M.; Yabu, K.; Nishi, T.; Yanagisawa, H.; Kanai, M.; Shibasaki, M. Synlett 2003, 353.
71. (a) Yabu, K.; Masumoto, S.; Kanai, M.; Curran, D. P.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 2923.
72. (b) Yabu, K.; Masumoto, S.; Kanai, M.; Shibasaki, M. Heterocycles 2003, 59, 369.
73. (a) Masumoto, S.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 8647.
74. (b) Masumoto, S.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron 2004, 60, 10497.
75. For reviews, see: (a) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517.
76. (b) Ohfune, Y.; Shinada, T. Bull. Chem. Soc. Jpn. 2003, 76, 1115.
77. (a) Gröger, H. Chem. Rev. 2003, 103, 2795.
78. (b) Spino, C. Angew. Chem. Int. Ed. 2004, 43, 1764.
79. (a) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
80. (b) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
81. Chavarot, M.; Byrne, J. J.; Chavant, P. Y.; Vallée, Y. Tetrahedron: Asymmetry 2001, 12, 1147.
82. Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634.
83. Kato, N.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2004, 45, 3147.
84. Kato, N.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2004, 45, 3153.
85. Trost, B. M.; Brown, B. S.; McEachern, E. J.; Kuhn, O. Chem.-Eur. J. 2003, 9, 4442.
86. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
87. Kato, N.; Tomita, D.; Maki, K.; Kanai, M.; Shibasaki, M. J. Org. Chem. 2004, 69, 6128.
88. Chiral ligands are commercially available from Junsei Chemical Co., Ltd. [fax: +81 (3)32705461].
89. Recently, Jacobsen reported a catalytic enantioselective acyl-Pictet-Spengler reaction: Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558.