Palladium-catalyzed synthesis of a phosphine oxide with a chiral phosphorus center via C-H phosphination

Heterocycles

Volumn 85, Issue 12, 2012, Pages 3029-3034

  Kuninobu, Yoichiro ^a,b   Origuchi, Kazuki ^a   Takai, Kazuhiko ^a  

^a OKAYAMA UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84870278078     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-12-12595     Document Type: Article

References (16)

1. For several examples of chiral phosphine oxides, see: (a) S. Hanessian, A. Gomtsyan, A. Payne, Y. Hervé, and S. Beaudoin, J. Org. Chem., 1993, 58, 5032;
2. (b) S. E. Denmark and S. I. Rivera, J. Org. Chem., 1994, 59, 6887;
3. (c) B. Faure, O. Pardigon, and G. Buono, Tetrahedron, 1997, 53, 11577;
4. (d) S. Matsukawa, H. Sugama, and T. Imamoto, Tetrahedron Lett., 2000, 41, 6461;
5. (e) H. Adams, R. C. Collins, S. Jones, and C. J. A. Warner, Org. Lett., 2011, 13, 6576.
6. (a) A. Bader, M. Pabel, and S. B. Wild, J. Chem. Soc., Chem. Commun., 1994, 1405;
7. (b) H. Yang, N. Lugan, and R. Mathieu, Organometallics, 1997, 16, 2089;
8. (c) B. Faure, O. Pardigon, and G. Buono, Tetrahedron, 1997, 53, 11577;
9. (d) T. Imamoto, J. Watanabe, Y. Wada, H. Masuda, H. Yamada, H. Tsuruta, S. Matsukawa, and K. Yamaguchi, J. Am. Chem. Soc., 1998, 120, 1635;
10. (e) T. Imamoto, J. Synth. Org. Chem., 2007, 65, 1060;
11. (f) T. Ogura, K. Yoshida, A. Yanagisawa, and T. Imamoto, Org. Lett., 2009, 11, 2245;
12. (g) T. Imamoto, K. Tamura, Z. Zhang, Y. Horiuchi, M. Sugiya, K. Yoshida, A. Yanagisawa, and I. D. Gridnev, J. Am. Chem. Soc., 2012, 134, 1754.
13. Y. Kuninobu, T. Yoshida, and K. Takai, J. Org. Chem., 2011, 76, 7370.
14. The reduction of phosphine oxide 2a was carried out according to the following reference: T. Nishimura, Y. Maeda, and T. Hayashi, Org. Lett., 2011, 13, 3674.
15. C.-W. Li, C.-I. Wang, H.-Y. Liao, R. Chaudhuri, and R.-S. Liu, J. Org. Chem., 2007, 72, 9203.
16. A. Velian, S. Lin, A. J. M. Miller, M. W. Day, and T. Agapie, J. Am. Chem. Soc., 2010, 132, 6296.