Asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated aldehydes catalyzed by a chiral diene-rhodium complex

Chemistry Letters

Volumn 34, Issue 11, 2005, Pages 1480-1481

  Hayashi, Tamio ^a   Tokunaga, Norihito ^a   Okamoto, Kazuhiro ^a   Shintani, Ryo ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 30144442471     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.1480     Document Type: Article

References (22)

1. a) T. Hayashi, K. Ueyama, N. Tokunaga, and K. Yoshida, J. Am. Chem. Soc., 125, 11508 (2003).
2. b) Y. Otomaru, K. Okamoto, R. Shintani, and T. Hayashi, J. Org. Chem., 70, 2503 (2005).
3. c) Y. Otomaru, A. Kina, R. Shintani, and T. Hayashi, Tetrahedron: Asymmetry, 16, 1673 (2005).
4. a) C. Fischer, C. Defieber, T. Suzuki, and E. M. Carreira, J. Am. Chem. Soc., 126, 1628 (2004).
5. b) C. Defieber, J.-F. Paquin, S. Serna, and E. M. Carreira, Org. Lett., 6, 3873 (2004).
6. c) F. Läng, F. Breher, D. Stein, and H. Grützmacher, Organometallics, 24, 2997 (2005).
7. a) N. Tokunaga, Y. Otomaru, K. Okamoto, K. Ueyama, R. Shintani, and T. Hayashi, J. Am. Chem. Soc., 126, 13584 (2004).
8. b) Y. Otomaru, N. Tokunaga, R. Shintani, and T. Hayashi, Org. Lett., 7, 307 (2005).
9. a) R. Shintani, K. Ueyama, I. Yamada, and T. Hayashi, Org. Lett., 6, 3425 (2004).
10. b) R. Shintani, T. Kimura, and T. Hayashi, Chem. Commun., 2005, 3213.
11. a) R. Shintani, K. Okamoto, Y. Otomaru, K. Ueyama, and T. Hayashi, J. Am. Chem. Soc., 127, 54 (2005).
12. b) R. Shintani, A. Tsurusaki, K. Okamoto, and T. Hayashi, Angew. Chem., Int. Ed., 44, 3909 (2005).
13. M. Ueda and N. Miyaura, J. Org. Chem., 65, 4450 (2000).
14. Rhodium-catalyzed 1,4-addition to enals has been also reported with organotin reagents: S. Oi, M. Moro, H. Ito, Y. Honma, S. Miyano, and Y. Inoue, Tetrahedron, 58, 91 (2002).
15. R. Itooka, Y. Iguchi, and N. Miyaura, J. Org. Chem., 68, 6000 (2003).
16. J.-F. Paquin, C. Defieber, C. R. J. Stephenson, and E. M. Carreira, J. Am. Chem. Soc., 127, 10850 (2005).
17. T. Hayashi and K. Yamasaki, Chem. Rev., 103, 2829 (2003).
18. D +10.7 (c 2.0, benzene) for (S)-3am of 97% ee: A. I. Meyers and M. Shipman, J. Org. Chem., 56, 7098 (1991).
19. 4 into 3-phenylheptanol.
20. J.-G. Boiteau, A. J. Minnaard, and B. L. Feringa, J. Org. Chem., 68, 9481 (2003).
21. H. Takaya, K. Mashima, K. Koyano, M. Yagi, H. Kumobayashi, T. Taketomi, S. Akutagawa, and R. Noyori, J. Org. Chem., 51, 629 (1986).
22. D -17.3 (c 1.38, dichloromethane) for (R)-3bm of 93% ee: K. Tanaka and G. C. Fu, J. Org. Chem., 66, 8177 (2001).