Asymmetric hydrosilylation of ketones using trans-chelating chiral peralkylbisphosphine ligands bearing primary alkyl substituents on phosphorus atoms

Bulletin of the Chemical Society of Japan

Volumn 73, Issue 2, 2000, Pages 485-496

  Kuwano, Ryoichi ^a   Sawamura, Masaya ^b   Shirai, Junya ^a   Takahashi, Masatoshi ^a   Ito, Yoshihiko ^a  

^a KYOTO UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; PHOSPHINE DERIVATIVE; RHODIUM COMPLEX;

ARTICLE; CHIRALITY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0034089275     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.73.485     Document Type: Article

References (86)

1. For reviews: a) I. Ojima and K. Hirai, in "Asymmetric Synthesis," ed by J. D. Morrison, Academic Press, New York (1985), Vol. 5, p. 103.
2. b) H. Brunner, H. Nishiyama, and K. Itoh, in "Catalytic Asymmetric Synthesis," ed by I. Ojima, VCH Publishers, New York (1993), p. 303.
3. 2-nitrogen-based ligands, see: a) H. Brunner, R. Becker, and G. Rieple, Organometallics, 3, 1354 (1984).
4. b) H. Brunner and A. Kürzinger, J. Organomet. Chem., 346, 413 (1988).
5. c) H. Brunner and U. Obermann, Chem. Ber., 122, 499 (1989).
6. d) H. Brunner and P. Brandle, J. Organomet. Chem., 390, C81 (1990).
7. e) S. Gladiali, L. Pinna, D. G. Delogu, E. Graf, and H. Brunner, Tetrahedron: Asymmetry, 1, 937 (1990).
8. f) H. Brunner and P. Brandle, Tetrahedron: Asymmetry, 2, 919 (1991).
9. g) H. Nishiyama, H. Sakaguchi, T. Nakamura, M. Horihata, M. Kondo, and K. Itoh, Organometallics, 8, 846 (1989).
10. h) H. Nishiyama, M. Kondo, T. Nakamura, and K. Itoh, Organometallics, 10, 500 (1991).
11. i) H. Nishiyama, S. Yamaguchi, M. Kondo, and K. Itoh, J. Org. Chem., 57, 4306 (1992).
12. j) H. Nishiyama, S.-B. Park, and K. Itoh, Tetrahedron: Asymmetry, 3, 1029 (1992).
13. k) H. Nishiyama, S. Yamaguchi, S.-B. Park, and K. Itoh, Tetrahedron: Asymmetry, 4, 143 (1993).
14. 2-nitrogen-phosphine hybrid ligands, see: a) T. Hayashi, C. Hayashi, and Y. Uozumi, Tetrahedron: Asymmetry, 6, 2503 (1995).
15. b) Y. Nishibayashi, K. Segawa, K. Ohe, and S. Uemura, Organometallics, 14, 5486 (1995).
16. c) Y. Nishibayashi, K. Segawa, H. Takada, K. Ohe, and S. Uemura, Chem. Commun., 1996, 847.
17. d) Y. Nishibayashi, I. Takei, S. Uemura, and M. Hidai, Organometallics, 17, 3420 (1998).
18. e) L. M. Newmann, J. M. J. Williams, R. McCague, and G. A. Potter, Tetrahedron: Asymmetry, 7, 1597 (1996).
19. f) T. Langer, J. Janssen, and G. Helmchen, Tetrahedron: Asymmetry, 7, 1599 (1996).
20. g) A. Sudo, H. Yoshida, and K. Saigo, Tetrahedron: Asymmetry, 8, 3205 (1997).
21. h) S.-g. Lee, C. W. Lim, C. E. Song, and I. O. Kim, Tetrahedron: Asymmetry, 8, 4027 (1997).
22. With a nitrogen-selenium hybrid ligand, see: a) Y. Nishibayashi, J. D. Singh, K. Segawa, S.-i. Fukuzawa, and S. Uemura, J. Chem. Soc., Chem. Commun., 1994, 1375.
23. b) Y. Nishibayashi, K. Segawa, J. D. Singh, S. Fukuzawa, K. Ohe, and S. Uemura, Organometallics, 15, 370 (1996).
24. With chiral phosphine ligands, see: a) W. Dumont, J.-C. Poulin, T.-P. Dang, and H. B. Kagan, J. Am. Chem. Soc., 95, 8295 (1973).
25. b) R. J. P. Corriu and J. J. E. Moreau, J. Organomet. Chem., 85, 19 (1975).
26. c) T. Hayashi, K. Yamamoto, K. Kasuga, H. Omizu, and M. Kumada, J. Organomet. Chem., 113, 127 (1976).
27. d) I. Ojima, T. Kogure, M. Kumagai, S. Horiuchi, and T. Sata, J. Organomet. Chem., 122, 83 (1976).
28. With chiral monophosphonite ligands, see: a) J.-i. Sakaki, W. B. Schweizer, and D. Seebach, Helv. Chem. Acta, 76, 2654 (1993).
29. b) D. Haag, J. Runsink, and H.-D. Scharf, Organometallics, 17, 398 (1998).
30. Highly enantioselective hydrosilylations of simple ketones using cis-chelating bisphosphines were reported by Imamoto very recently, see: a) H. Tsuruta and T. Imamoto, Tetrahedron: Asymmetry, 10, 877 (1999).
31. b) Y. Yamanoi and T. Imamoto, J. Org. Chem., 64, 2988 (1999).
32. For asymmetric hydrosilylation of keto esters, see: I. Ojima, T. Kogure, and M. Kumagai, J. Org. Chem., 42, 1671 (1977).
33. For asymmetric intramolecular hydrosilylation, see: M. J. Burk and J. E. Feaster, Tetrahedron Lett., 33, 2099 (1992).
34. TRAP=trans-chelating chiral bisphosphine: a) M. Sawamura, H. Hamashima, and Y. Ito, Tetrahedron: Asymmetry, 2, 593 (1991).
35. b) M. Sawamura, H. Hamashima, M. Sugawara, R. Kuwano, and Y. Ito, Organometallics, 14, 4549 (1995).
36. c) R. Kuwano, M. Sawamura, S. Okuda, T. Asai, Y. Ito, M. Redon, and A. Krief, Bull. Chem. Soc. Jpn., 70, 2807 (1998).
37. Preliminary communications: a) M. Sawamura, R. Kuwano, and Y. Ito, Angew. Chem., Int. Ed. Engl., 33, 111 (1994).
38. b) M. Sawamura, R. Kuwano, J. Shirai, and Y. Ito, Synlett, 1995, 347.
39. c) R. Kuwano, M. Sawamura, J. Shirai, M. Takahashi, and Y. Ito, Tetrahedron Lett., 36, 5239 (1995).
40. R. Kuwano, T. Uemura, M. Saitoh, and Y. Ito, Tetrahedron Lett., 40, 1327 (1999).
41. For recent reviews, see: a) I. Ojima, "Catalytic Asymmetric Synthesis," VCH Publishers, New York (1993).
42. b) H. Brunner and W. Zettlmeier, "Handbook of Enantioselective Catalysis with Transition Metal Compounds," VCH Publishers, Weinheim (1993), Vol. I and II.
43. c) R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wiley & Sons, New York (1994).
44. EtDIOP=2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diethylphosphino) butane: a) K. Tani, K. Suwa, T. Yamagata, and S. Otsuka, Chem. Lett., 1982, 265.
45. b) K. Tani, K. Suwa, E. Tanigawa, T. Ise, T. Yamagata, Y. Tatsuno, and S. Otsuka, J. Organomet. Chem., 370, 203 (1989).
46. K. Tani, T. Yamagata, S. Akutagawa, H. Kumobayashi, T. Taketomi, H. Takaya, A. Miyashita, R. Noyori, and S. Otsuka, J. Am. Chem. Soc., 106, 5208 (1984).
47. a) Q. Jiang, Y. Jiang, D. Xiao, P. Cao, and X. Zhang, Angew. Chem., Int. Ed. Engl., 37, 1100 (1998).
48. b) T. Imai, T. Tamura, A. Yamamuro, T. Sato, T. A. Wollmann, R. M. Kennedy, and S. Masamune, J. Am. Chem. Soc., 108, 7402 (1986).
49. a) I. Ojima, T. Kogure, and Y. Nagai, Tetrahedron Lett., 1972, 5035.
50. b) I. Ojima and T. Kogure, Organometallics. 1, 1390 (1982).
51. c) T. Kogure and I. Ojima, J. Organomet. Chem., 234, 249 (1982).
52. For examples, see: a) R. Noyori, T. Ohkuma, M. Kitamura, H. Takaya, N. Sayo, H. Kumobayashi, and S. Akutagawa, J. Am. Chem. Soc., 109, 5856 (1987).
53. b) M. Kitamura, T. Ohkuma, S. Inoue, N. Sayo, H. Kumobayashi, S. Akutagawa, T. Ohta, H. Takaya, and R. Noyori, J. Am. Chem. Soc., 110, 629 (1988).
54. c) R. Noyori, T. Ikeda, T. Ohkuma, M. Widhalm, M. Kitamura, H. Takaya, S. Akutagawa, N. Sayo, T. Saito, T. Taketomi, and H. Kumobayashi, J. Am. Chem. Soc., 111, 9134 (1989).
55. Preferential formation of (2R,4R)-9b to (2S,4S)-9b might be caused by a dehydrogenative coupling of 8b with diphenylsilane. Based on the asymetric hydrosilylation of 3c (Table 4), the remaining carbonyl group of the resulting silyl enol ether, which is an α,β-unsaturated ketone, would be reduced with R-selectivity by diphenylsilane and (R,R)-(S,S)-alkylTRAP-rhodium caltalyst. (equation presented)
56. B. M. Trost, J. L. Belletire, S. Godleski, P. G. McDougal, J. M. Balkovec, J. J. Baldwin, M. E. Christy, G. S. Ponticello, S. L. Varga, and J. P. Spinger, J. Org. Chem., 51, 2370 (1986).
57. T. G. Shenck, J. M. Downs, C. R. C. Milne, P. B. Mackenzie, H. Boucher, J. Whealan, and B. Bosnich, Inorg. Chem., 24, 2334 (1985).
58. W. J. Bailey and M. Madoff, J. Am. Chem. Soc., 76, 2707 (1954).
59. F. C. Montgomery and W. H. Saunders, Jr., J. Org. Chem., 41, 2368 (1976).
60. H. C. Brown, J. Chandrasekharan, and P. V. Ramachandran, J. Am. Chem. Soc., 110, 1539 (1988).
61. R. Chong and P. S. Clezy, Aust. J. Chem., 20, 123 (1967).
62. O. Itoh, N. Iwakoshi, T. Saitoh, H. Katano, Y. Fujisawa, Y. Hasegawa, T. Sugita, and K. Ichikawa, Bull. Chem. Soc. Jpn., 55, 177 (1982).
63. R. A. Micheli, Z. G. Hajos, N. Cohen, D. R. Parrish, L. A. Portland, W. Sciamanna, M. A. Scott, and P. A. Wehrli, J. Org. Chem., 40, 675 (1975).
64. U. Nagai, T. Shishido, R. Chiba, and H. Mitsuhashi, Tetrahedron, 21, 1701 (1965).
65. T. Hayashi, Y. Matsumoto, and Y. Ito, Tetrahedron: Asymmetry, 2, 601 (1991).
66. K. Okamoto, T. Kinoshita, Y. Takemura, and H. Yoneda, J. Chem. Soc., Perkin Trans. 2, 1975, 1426.
67. C.-P. Chen, K. Prasad, and O. Repic, Tetrahedron Lett., 32, 7175 (1991).
68. S. G. Davies and C. L. Goodfellow, J. Chem. Soc., Perkin Trans. 1, 1989, 192.
69. T. Ishizaki, H. Miura, and H. Nohira, Nippon Kagaku Kaishi, 1980, 1381.
70. P. D. Theisen and C. H. Heathcock, J. Org. Chem., 53, 2374 (1988).
71. G. Gokel, D. Marquarding, and I. Ugi, J. Org. Chem., 37, 3052 (1972).
72. G. Jaouen and A. Meyer, J. Am. Chem. Soc., 97, 4667 (1975).
73. A. G. Davies and A. M. White, J. Chem. Soc., 1952, 3300.
74. H. Kwart and D. P. Hoster, J. Org. Chem., 32, 1867 (1967).
75. P. A. Levene and L. A. Mikeska, J. Biol. Chem., 75, 587 (1927).
76. R. H. Pickard and J. Kenyon, J. Chem. Soc., 103, 1923 (1913).
77. R. H. Pickard and J. Kenyon, J. Chem. Soc., 105, 1115 (1914).
78. H. C. Brown, B. T. Cho, and W. S. Park, J. Org. Chem., 53, 1231 (1988).
79. S. Terashima, N. Tanno, and K. Koga, J. Chem. Soc., Chem. Commun., 1980, 1026.
80. J. Kenyon, S. M. Partridge, and H. Phillips, J. Chem. Soc., 1936, 85.
81. H. C. Brown and G. G. Pai, J. Org. Chem., 50, 1384 (1985).
82. B. Wipf, E. Kupfer, R. Bertazzi, and G. W. Leuenberger, Helv. Chem. Acta, 66, 485 (1983).
83. K. Mori, Tetrahedron, 31, 3011 (1975).
84. J. J. Plattner and H. Rapoport, J. Am. Chem. Soc., 93, 1758 (1971).
85. T. Tanabe, Bull. Chem. Soc. Jpn., 46, 2233 (1973).
86. M. J. Burk, J. E. Feaster, and R. L. Harlow, Tetrahedron: Asymmetry, 2, 569 (1991).