Rhodium-catalyzed asymmetric 1,4-addition of alkenylsilanes generated by hydrosilylation of alkynes: A one-pot procedure where a rhodium/(S)-binap complex catalyzes the two successive reactions

Tetrahedron Asymmetry

Volumn 15, Issue 17, 2004, Pages 2647-2651

  Otomaru, Yusuke ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; ALKYNE DERIVATIVE; KETONE DERIVATIVE; RHODIUM; SILANE DERIVATIVE; TRIETHOXYSILANE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; COMPLEX FORMATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SILYLATION;

EID: 4444276235     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.07.003     Document Type: Article

References (43)

1. For reviews: T. Hayashi Synlett 9 2001 879
2. K. Fagnou, and M. Lautens Chem. Rev. 103 2003 169
3. T. Hayashi, and K. Yamasaki Chem. Rev. 103 2003 2829
4. Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura J. Am. Chem. Soc. 120 1998 5579
5. Y. Takaya, T. Senda, H. Kurushima, M. Ogasawara, and T. Hayashi Tetrahedron: Asymmetry 10 1999 4047
6. Y. Takaya, M. Ogasawara, and T. Hayashi Tetrahedron Lett. 40 1999 6957
7. T. Hayashi, T. Senda, Y. Takaya, and M. Ogasawara J. Am. Chem. Soc. 121 1999 11591
8. T. Hayashi, T. Senda, and M. Ogasawara J. Am. Chem. Soc. 122 2000 10716
9. T. Senda, M. Ogasawara, and T. Hayashi J. Org. Chem. 66 2001 6852
10. T. Hayashi, M. Takahashi, Y. Takaya, and M. Ogasawara J. Am. Chem. Soc. 124 2002 5052
11. S. Sakuma, M. Sakai, R. Itooka, and N. Miyaura J. Org. Chem. 65 2000 5951
12. S. Sakuma, and N. Miyaura J. Org. Chem. 66 2001 8944
13. M. Kuriyama, and K. Tomioka Tetrahedron Lett. 42 2001 921
14. M. Kuriyama, K. Nagai, K.-i. Yamada, Y. Miwa, T. Taga, and K. Tomioka J. Am. Chem. Soc. 124 2002 8932
15. M.T. Reetz, D. Moulin, and A. Gosberg Org. Lett. 3 2001 4083
16. R. Amengual, V. Michelet, and J.-P. Genêt Synlett 2002 1791
17. M. Pucheault, S. Darses, and J.-P. Genêt Tetrahedron Lett. 43 2002 6155
18. M. Pucheault, S. Darses, and J.-P. Genêt Eur. J. Org. Chem. 2002 3552
19. Q. Shi, L. Xu, X. Li, X. Jia, R. Wang, T.T.-L. Au-Yeung, A.S.C. Chan, T. Hayashi, R. Cao, and M. Hong Tetrahedron Lett. 44 2003 6505
20. J.-G. Boiteau, R. Imbos, A.J. Minnaard, and B.L. Feringa Org. Lett. 5 2003 681 and Org. Lett. 2003, 5, 1385 for corrections
21. J.-G. Boiteau, A.J. Minnaard, and B.L. Feringa J. Org. Chem. 68 2003 9481
22. Y. Ma, C. Song, C. Ma, Z. Sun, Q. Chai, and M.B. Andrus Angew. Chem., Int. Ed. 42 2003 5871
23. T. Hayashi, N. Tokunaga, K. Yoshida, and J.W. Han J. Am. Chem. Soc. 124 2002 12102
24. K. Yoshida, and T. Hayashi J. Am. Chem. Soc. 125 2003 2872
25. S. Oi, A. Taira, Y. Honma, and Y. Inoue Org. Lett. 5 2003 97
26. For the nonasymmetric version of rhodium-catalyzed 1,4-addition: A. Mori, Y. Danda, T. Fujii, K. Hirabayashi, and K. Osakada J. Am. Chem. Soc. 123 2001 10774
27. T.-S. Huang, and C.-J. Li Chem. Commun. 2001 2348
28. T. Koike, X. Du, A. Mori, and K. Osakada Synlett 2002 301
29. S. Oi, Y. Honma, and Y. Inoue Org. Lett. 4 2002 667
30. M. Murata, R. Shimazaki, M. Ishikura, S. Watanabe, and Y. Masuda Synthesis 2002 717
31. T. Hayashi, K. Ueyama, N. Tokunaga, and K. Yoshida J. Am. Chem. Soc. 125 2003 11508
32. Y. Takaya, M. Ogasawara, and T. Hayashi Tetrahedron Lett. 39 1998 8479
33. For the rhodium-catalyzed hydrosilylation of alkynes: I. Ojima, and M. Kumagai J. Organomet. Chem. 66 1974 C14
34. H. Watanabe, T. Kitahara, T. Motegi, and Y. Nagai J. Organomet. Chem. 139 1977 215
35. R. Takeuchi, and N. Tanouchi J. Chem. Soc., Perkin Trans. 1 1994 2909
36. R. Takeuchi, S. Nitta, and D. Watanabe J. Org. Chem. 60 1995 3045
37. A. Mori, E. Takahisa, H. Kajiro, K. Hirabayashi, Y. Nishihara, and T. Hiyama Chem. Lett. 1998 443
38. J.W. Faller, and D.G. D'Alliessi Organometallics 21 2002 1743
39. G.H. Barnes, and N.E. Daughenbaugh J. Org. Chem. 31 1966 885
40. K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 16 1975 4467
41. T.X. Neenan, and G.M. Whitesides J. Org. Chem. 53 1988 2489
42. B. Patro, B. Deb, H. Ila, and H. Junjappa J. Org. Chem. 57 1992 2257
43. H. Hiemstra, and H. Wynberg Tetrahedron Lett. 18 1977 2183