Chiral lithium salts of phosphoric acids as Lewis acid-base conjugate catalysts for the enantioselective cyanosilylation of ketones

Advanced Synthesis and Catalysis

Volumn 350, Issue 11-12, 2008, Pages 1776-1780

  Hatano, Manabu ^a   Ikeno, Takumi ^a   Matsumura, Tokihiko ^a   Torii, Shinobu ^a   Ishihara, Kazuaki ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Asymmetric catalysis; Cyanohydrins; Cyanosilylation; Ketones; Lithium; Phosphoric acids

Indexed keywords

EID: 53849117116     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800314     Document Type: Article

References (75)

1. Reviews for cyanohydrin synthesis: a) M. North, Synlett 1993, 807;
2. b) F. Effenberger, Angew. Chem. 1994, 106, 1609;
3. Angew. Chem. Int. Ed. Engl. 1994, 33, 1555;
4. c) M. North, Tetrahedron: Asymmetry 2003, 14, 147;
5. d) J.-M. Brunel, I. P. Holmes, Angew. Chem. 2004, 116, 2810;
6. Angew. Chem. Int. Ed. 2004, 43, 2752.
7. For a recent review, see: M. Hatano, K. Ishihara, Synthesis 2008, 1647.
8. R. J. H. Gregory, Chem. Rev. 1999, 99, 3649.
9. Chiral salen-Ti(IV) catalysts: a) Y. N. Belokon, B. Green, N. S. Ikonnikov, M. North, V. I. Tararov, Tetrahedron Lett. 1999, 40, 8147;
10. b) Y. N. Belokon, B. Green, N. S. Ikonnikov, M. North, T. Parsons, V. I. Tararov, Tetrahedron 2001, 57, 771;
11. c) T. R. J. Achard, L. A. Clutterbuck, M. North, Synlett 2005, 1828.
12. Chiral Ti(IV) or Al(III)/N-oxide catalysts: a) Y. Shen, X. Feng, G. Zhang, Y. Jiang, Synlett 2002, 1353;
13. b) F. Chen, X. Feng, B. Qin, G. Zhang, Y. Jiang, Org. Lett. 2003, 5, 949;
14. c) Y. Shen, X. Feng, Y. Li, G. Zhang, Y. Jiang, Eur. J. Org. Chem. 2004, 129;
15. d) B. He, F.-X. Chen, Y. Li, X. Feng, G. Zhang, Tetrahedron Lett. 2004, 45, 5465;
16. e) B. He, F.-X. Chen, Y. Li, X. Feng, G. Zhang, Eur. J. Org. Chem. 2004, 4657;
17. f) F.-X. Chen, B. Qin, X. Feng, G. Zhang, Y. Jiang, Tetrahedron 2004, 60, 10449;
18. g) F.-X. Chen, H. Zhou, X. Liu, B. Qin, X. Feng, G. Zhang, Y. Jiang, Chem. Eur. J. 2004, 10, 4790;
19. h) A. Alaaeddine, T. Roisnel, C. M. Thomas, J.-F. Carpentier, Adv. Synth. Catal. 2008, 350, 731.
20. Chiral peptide-Al(III) catalysts: H. Deng, M. P. Isler, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 2002, 114, 1051;
21. Angew. Chem. Int. Ed. 2002, 41, 1009.
22. Chiral N-oxide catalysts: B. Qin, X. Liu, J. Shi, K. Zheng, H. Zhao, X. Feng, J. Org. Chem. 2007, 72, 2374.
23. Cinchona alkaloid catalysts: S.-K. Tian, R. Hong, L. Deng, J. Am. Chem. Soc. 2003, 125, 9900.
24. Chiral oxazaborolidinium catalysts: D. H. Ryu, E. J. Corey, J. Am. Chem. Soc. 2005, 127, 5384.
25. Chiral thiourea catalysts: a) D. E. Fuerst, E. N. Jacobsen, J. Am. Chem. Soc. 2005, 127, 8964;
26. b) S. J. Zuend, E. N. Jacobsen, J. Am. Chem. Soc. 2007, 129, 15872.
27. Chiral N,N-Ti(IV) catalysts: a) Y. Xiong, X. Huang, S. Gou, J. Huang, Y. Wen, X. Feng, Adv. Synth. Catal. 2006, 348, 538;
28. b) Q. Li, X. Liu, J. Wang, K. Shen, X. Feng, Tetrahedron Lett. 2006, 47, 4011;
29. c) K. Shen, X. Liu, Q. Li, X. Feng, Tetrahedron 2008, 64, 147.
30. Chiral salen-metal catalysts: a) S. S. Kim, S. H. Lee, J. M. Kwak, Tetrahedron: Asymmetry 2006, 17, 1165;
31. b) S. S. Kim, Pure Appl. Chem. 2006, 78, 977.
32. Chiral amino acid salts: X. Liu, B. Qin, X. Zhou, B. He, X. Feng, J. Am. Chem. Soc. 2005, 127, 12224.
33. I. P. Holmes, H. B. Kagan, Tetrahedron Lett. 2000, 41, 7453.
34. M. Hatano, T. Ikeno, T. Miyamoto, K. Ishihara, J . Am. Chem. Soc. 2005, 127, 10776.
35. Kagan reported catalytic enantioselective hydrosilylation of acetophenone with a Li salt of (R)-binaphthylphosphoric acid (37%, 6% ee): R. Schiffres, H. B. Kagan, Synlett 1997, 1175.
36. K. Ishihara, A. Sakakura, M. Hatano, Synlett 2007, 686.
37. a) M. Hatano, T. Miyamoto, K. Ishihara, Adv. Synth. Catal. 2005, 347, 1561;
38. b) M. Hatano, T. Miyamoto, K. Ishihara, Synlett 2006, 1762;
39. c) M. Hatano, T. Miyamoto, K. Ishihara, J. Org. Chem. 2006, 71, 6474;
40. d) M. Hatano, T. Miyamoto, K. Ishihara, Org. Lett. 2007, 9, 4535.
41. Pioneering works of bifunctional catalysts with the P=O moiety by Shibasaki: a) Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641;
42. b) M. Kanai, Y. Hamashima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 2405;
43. c) Y. Hamashima, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 7412;
44. d) Y. Hamashima, M. Kanai, M. Shibasaki, Tetrahedron Lett. 2001, 42, 691;
45. e) K. Yabu, S. Masumoto, S. Yamasaki, Y. Hamashima, M. Kanai, W. Du, D. P. Curran, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 9908;
46. f) S. Masumoto, K. Yabu, M. Kanai, M. Shibasaki, Tetrahedron Lett. 2002, 43, 2919;
47. g) K. Yabu, S. Masumoto, M. Kanai, D. P. Curran, M. Shibasaki, Tetrahedron Lett. 2002, 43, 2923;
48. h) S. Masumoto, M. Suzuki, M. Kanai, M. Shibasaki, Tetrahedron Lett. 2002, 43, 8647;
49. i) K. Fujii, K. Maki, M. Kanai, M. Shibasaki, Org. Lett. 2003, 5, 733;
50. j) K. Yabu, S. Masumoto, M. Kanai, W. Du, D. P. Curran, M. Shibasaki, Heterocycles 2003, 59, 369;
51. k) N. Kato, D. Tomita, K. Maki, M. Kanai, M. Shibasaki, J. Org. Chem. 2004, 69, 6128;
52. l) S. Masumoto, M. Suzuki, M. Kanai, M. Shibasaki, Tetrahedron 2004, 60, 10497.
53. a) M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187;
54. b) M. Shibasaki, M. Kanai, K. Funabashi, Chem. Commun. 2002, 1989;
55. c) M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Pure Appl. Chem. 2005, 77, 2047;
56. d) M. Shibasaki, M. Kanai, Org. Biomol. Chem. 2007, 5, 2027;
57. e) M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett 2005, 1491.
58. E. M. Arnett, E. J. Mitchell, T. S. S. R. Murty, J. Am. Chem. Soc. 1974, 96, 3875.
59. a) C. Chuit, R. J. P. Corriu, C. Reye, J. C. Young, Chem. Rev. 1993, 93, 1371;
60. b) S. Rendler, M. Oestreich, Synthesis 2005, 1727;
61. c) Y. Orito, M. Nakajima, Synthesis 2006, 1391.
62. Pioneering work of asymmetric catalysis using the BINOL-derived chiral phosphoric acid compounds: a) H. Alper, N. Hamel, J. Am. Chem. Soc. 1990, 112, 2803;
63. b) J. Inanaga, Y. Sugimoto, T. Hanamoto, New J. Chem. 1995, 19, 707;
64. c) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592;
65. Angew. Chem. Int. Ed. 2004, 43, 1566;
66. d) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356;
67. also see the review and the references in: e) T. Akiyama, Chem. Rev. 2007, 107, 5744.
68. a) G. B. Rowland, H. Zhang, E. B. Rowland, S. Chennamadhavuni, Y. Wang, J. C. Antilla, J. Am. Chem. Soc. 2005, 127, 15696;
69. b) M. Rueping, E. Sugiono, C. Azap, T. Theissmann, M. Bolte, Org. Lett. 2005, 7, 3781;
70. c) S. Hoffmann, A. M. Seayad, B. List, Angew. Chem. 2005, 117, 7590;
71. Angew. Chem. Int. Ed. 2005, 44, 7424;
72. d) R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84;
73. e) G. L. Hamilton, E. J. Kang, M. Mba, F. D. Toste, Science 2007, 317, 496.
74. The reactions could not proceed without n-BuLi.
75. [15] [27] The unexpected reversal of the absolute enantioselectivity is not fully understood and further examinations are necessary. However, not only steric and electric factors, but also an aggregation structure of lithium salts should be involved.