Catalytic enantioselective synthesis of alkenylhydrosilanes

Angewandte Chemie - International Edition

Volumn 51, Issue 51, 2012, Pages 12745-12748

  Igawa, Kazunobu ^a   Yoshihiro, Daisuke ^a   Ichikawa, Nobumasa ^a   Kokan, Naoto ^b   Tomooka, Katsuhiko ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

asymmetric synthesis; enantioselectivity; hydrosilylation; ozone; silanes

Indexed keywords

ALKENYL; ASYMMETRIC CATALYSTS; ASYMMETRIC SYNTHESIS; CHIRAL BUILDING BLOCKS; DESYM-METRIZATION; ENANTIOSELECTIVE SYNTHESIS; FUNCTIONALIZED; STEREO-SELECTIVE;

ACETYLENE; ENANTIOSELECTIVITY; HYDROSILYLATION; OZONE; SILANES;

CHELATION;

EID: 84870313675     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201207361     Document Type: Article

References (56)

1. L. H. Sommer, Stereochemistry, Mechanism and Silicon, McGraw-Hill, New York, 1965
2. R. J. P. Corriu, C. Guérin, J. J. E. Moreau, in Topics in Stereochemistry, Vol. 15 (Ed.:, E. L. Eliel,), Wiley, New York, 1984, pp. 43-198
3. M. A. Brook, in Silicon in Organic, Organometallic, and Polymer Chemistry, Wiley, New York, 2000, pp. 115-137
4. T. Murafuji, K. Kurotobi, N. Nakamura, Y. Sugihara, Curr. Org. Chem. 2002, 6, 1469
5. A. Weickgenannt, M. Mewald, M. Oestreich, Org. Biomol. Chem. 2010, 8, 1497
6. L.-W. Xu, L. Li, G.-Q. Lai, J.-X. Jiang, Chem. Soc. Rev. 2011, 40, 1777.
7. For a representative review on the application of nonracemic silanes to material chemistry, see:, Y. Kawakami, Y. Kakihana, O. Ooi, M. Oishi, K. Suzuki, S. Shinke, K. Uenishi, Polym. Int. 2009, 58, 279, and references therein.
8. For a representative review on the application of nonracemic silanes to bioorganic chemistry, see:, W. Bains, R. Tacke, Curr. Opin. Drug Discovery Dev. 2003, 6, 526, and references therein.
9. K. Tomooka, A. Nakazaki, T. Nakai, J. Am. Chem. Soc. 2000, 122, 408
10. K. Igawa, J. Takada, T. Shimono, K. Tomooka, J. Am. Chem. Soc. 2008, 130, 16132
11. A. Nakazaki, J. Usuki, K. Tomooka, Synlett 2008, 2064.
12. A. Nakazaki, T. Nakai, K. Tomooka, Angew. Chem. 2006, 118, 2293
13. Angew. Chem. Int. Ed. 2006, 45, 2235
14. K. Igawa, N. Kokan, K. Tomooka, Angew. Chem. 2010, 122, 740
15. Angew. Chem. Int. Ed. 2010, 49, 728.
16. R. J. P. Corriu, J. J. E. Moreau, Tetrahedron Lett. 1973, 14, 4469
17. D. R. Schmidt, S. J. O'Malley, J. L. Leighton, J. Am. Chem. Soc. 2003, 125, 1190; for Si-O bond-forming hydrosilylation with ketones, see
18. R. J. P. Corriu, J. J. E. Moreau, J. Organomet. Chem. 1974, 64, C 51
19. T. Hayashi, K. Yamamoto, M. Kumada, Tetrahedron Lett. 1974, 15, 331
20. R. J. P. Corriu, J. J. E. Moreau, J. Organomet. Chem. 1975, 85, 19
21. T. Ohta, M. Ito, A. Tsuneto, H. Takaya, J. Chem. Soc. Chem. Commun. 1994, 2525; for metal carbenoid insertion into the Si-H bond, see
22. Y. Yasutomi, H. Suematsu, T. Katsuki, J. Am. Chem. Soc. 2010, 132, 4510.
23. A. H. Djerourou, L. Blanco, Tetrahedron Lett. 1991, 32, 6325
24. A. H. Djerourou, L. Blanco, Phosphorus Sulfur Silicon Relat. Elem. 1999, 149, 107; for the asymmetric desymmetrization of silacyclobutanes, see
25. R. Shintani, K. Moriya, T. Hayashi, J. Am. Chem. Soc. 2011, 133, 16440
26. R. Shintani, K. Moriya, T. Hayashi, Org. Lett. 2012, 14, 2902; for the desymmetric C-H bond functionalization of achiral triarylsilanes, see
27. R. Shintani, H. Otomo, K. Ota, T. Hayashi, J. Am. Chem. Soc. 2012, 134, 7305; for the desymmetric transmetalation of achiral triarylsilanes, see
28. R. Shintani, E. E. Maciver, F. Tamakuni, T. Hayashi, J. Am. Chem. Soc. 2012, 134, 16955.
29. R. Tacke, K. Fritsche, A. Tafel, F. Wuttke, J. Organomet. Chem. 1990, 388, 47
30. R. Tacke, S. Brakmann, F. Wuttke, J. Organomet. Chem. 1991, 403, 29
31. N. E. Aouf, A. H. Djerourou, L. Blanco, Phosphorus Sulfur Silicon Relat. Elem. 1994, 88, 207
32. T. Fukui, T. Kawamoto, A. Tanaka, Tetrahedron: Asymmetry 1994, 5, 73
33. R. Tacke, T. Heinrich, Silicon Chem. 2002, 1, 35; for resolution by HPLC using a chiral stationary phase, see
34. R. Tacke, D. Reichel, K. Günther, S. Merget, Z. Naturforsch. B 1995, 50, 568
35. A. Mori, F. Toriyama, H. Kajiro, K. Hirabayashi, Y. Nishihara, T. Hiyama, Chem. Lett. 1999, 549
36. T. Schmid, J. O. Daiss, R. Ilg, H. Surburg, R. Tacke, Organometallics 2003, 22, 4343.
37. D. Seebach, M. Hayakawa, J. Sakaki, W. B. Schweizer, Tetrahedron 1993, 49, 1711
38. J. Sakaki, W. B. Schweizer, D. Seebach, Helv. Chim. Acta 1993, 76, 2654.
39. For a recent review on the taddol-derived phosphonite ligand, see:, H. W. Lam, Synthesis 2011, 2011.
40. H. E. Burks, L. T. Kliman, J. P. Morken, J. Am. Chem. Soc. 2009, 131, 9134
41. L. T. Kliman, S. N. Mlynarski, J. P. Morken, J. Am. Chem. Soc. 2009, 131, 13210.
42. Oestreich and colleagues reported the kinetic resolution of chiral alcohols by dehydrogenative Si-O coupling using a Cu catalyst with taddol-derived phosphonite ligands:, A. Weickgenannt, M. Mewald, T. W. T. Muesmann, M. Oestreich, Angew. Chem. 2010, 122, 2269
43. Angew. Chem. Int. Ed. 2010, 49, 2223.
44. T. Kusumoto, T. Hiyama, Chem. Lett. 1985, 1405
45. S. J. Lee, M. K. Park, B. H. Han, Silicon Chem. 2002, 1, 41
46. T. Takahashi, F. Bao, G. Gao, M. Ogasawara, Org. Lett. 2003, 5, 3479
47. A. Corma, C. González-Arellano, M. Iglesias, F. Sánchez, Angew. Chem. 2007, 119, 7966
48. Angew. Chem. Int. Ed. 2007, 46, 7820
49. J. Montenegro, J. Bergueiro, C. Saá, S. López, Org. Lett. 2009, 11, 141
50. Y. Sumida, T. Kato, S. Yoshida, T. Hosoya, Org. Lett. 2012, 14, 1552.
51. 3] and phosphonite ligands 6 a and 6 c were prepared according to the procedures of Morken et al.; see: Ref. [11]. For related additions and corrections, see:, H. E. Burks, L. T. Kliman, J. P. Morken, J. Am. Chem. Soc. 2010, 132, 13949.
52. L. H. Sommer, J. E. Lyons, H. Fujimoto, J. Am. Chem. Soc. 1969, 91, 7051.
53. A. G. Brook, K. H. Pannell, D. G. Anderson, J. Am. Chem. Soc. 1968, 90, 4374.
54. M. Murakami, K. Sakita, K. Igawa, K. Tomooka, Org. Lett. 2006, 8, 4023
55. K. Igawa, K. Sakita, M. Murakami, K. Tomooka, Synthesis 2008, 1641
56. K. Igawa, Y. Kawasaki, K. Tomooka, Chem. Lett. 2011, 40, 233.