Chiral bisphospholane ligands (Me-ketalphos): Synthesis of their Rh(I) complexes and applications in asymmetric hydrogenation

Tetrahedron

Volumn 62, Issue 5, 2006, Pages 868-871

  Dai, Qian ^a   Wang, Chun Jiang ^a   Zhang, Xumu ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

Catalyst; Hydrogenation; Rhodium

Indexed keywords

ALKENE DERIVATIVE; PHOSPHINE DERIVATIVE; RHODIUM COMPLEX;

ARTICLE; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; PRECURSOR; PRIORITY JOURNAL; SYNTHESIS;

EID: 29144513854     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.10.047     Document Type: Article

References (30)

1. H. Brunner, and W. Zettlmeier Handbook of Enantioselective Catalysis with Transition Metal Compounds Vol. 2 1993 VCH Verlagsgesellschaft Weinheim Ligands-References, p 359
2. M.J. Burk, J.E. Feaster, and R.L. Harlow Organometallics 9 1990 2653
3. M.J. Burk J. Am. Chem. Soc. 113 1991 8518
4. M.J. Burk, J.E. Feaster, W.A. Nugent, and R.L. Harlow J. Am. Chem. Soc. 115 1993 10125
5. M.J. Burk, J.R. Lee, and J.P. Martine J. Am. Chem. Soc. 116 1994 10847
6. M.J. Burk, Y.M. Wang, and J.R. Lee J. Am. Chem. Soc. 118 1996 5142
7. J. Holz, M. Quirmbach, U. Schmidt, D. Heller, R. Stürmer, and A. Börner J. Org. Chem. 63 1998 8031
8. J. Holz, R. Stürmer, U. Schmidt, H.-J. Drexler, D. Heller, H.-P. Krimmer, and A. Börner Eur. J. Org. Chem. 24 2001 4615
9. J. Holz, D. Heller, R. Stürmer, and A. Börner Tetrahedron Lett. 40 1999 7059
10. J. Holz, A. Monsees, H. Jiao, J. You, I.V. Komarov, C. Fischer, K. Drauz, and A. Borner J. Org. Chem. 68 2003 1701
11. W. Tang, and X. Zhang Chem. Rev. 103 2003 3029
12. D. Liu, W. Li, and X. Zhang Org. Lett. 4 2002 4471
13. W. Li, Z. Zhang, D. Xiao, and X. Zhang Tetrahedron Lett. 40 1999 6701
14. W. Li, Z. Zhang, D. Xiao, and X. Zhang J. Org. Chem. 65 2000 3489
15. S. Shin, and T.V. RajanBabu Org. Lett. 1 1999 1229
16. Y. Yan, and T.V. RajanBabu J. Org. Chem. 65 2000 900
17. T.V. RajanBabu, Y. Yan, and S. Shin J. Am. Chem. Soc. 123 2001 10207
18. H. Brunner Applied Homogeneous Catalysis with Organometallic compounds B. Cornils W.A. Herrmann 2nd ed. 2001 Wiley-VCH Weinheim 209
19. C.J. Cobley, I.C. Lennon, R. McCague, J.A. Ramsden, and A. Zannotti-Gerosa Tetrahedron Lett. 42 2001 7481
20. Phosphorus NMR showed that the complex was decomposed after certain period of time with detection of a small peak at 83 ppm.
21. The hydrogenation reaction was performed with 0.1 mol% loading of complex 4 at standard reaction condition for enamides for 16 h with 100% conversion.
22. The hydrogenation reaction was performed with 0.1 mol% loading of complex 4 at standard reaction condition for enamides for 2 h with 14% conversion.
23. D.A. Evans, F.E. Michael, J.S. Tedrow, and K.R. Campos J. Am. Chem. Soc. 125 2003 3534
24. A. Ohashi, and T. Imamoto Org. Lett. 3 2001 373
25. T. Imamoto, J. Watanabe, Y. Wada, H. Masuda, H. Yamada, H. Tsuruta, S. Matsukawa, and K. Yamaguchi J. Am. Chem. Soc. 120 1998 1635
26. M.J. Burk, M.F. Gross, and J.P. Martinez J. Am. Chem. Soc. 117 1995 9375
27. M. Sawamura, R. Kuwano, and Y. Ito J. Am. Chem. Soc. 117 1995 9602
28. G. Zhu, and X. Zhang J. Org. Chem. 63 1998 3133
29. W. Li, and X. Zhang J. Org. Chem. 65 2002 5871
30. S. Wu, W. Wang, W. Tang, M. Lin, and X. Zhang Org. Lett. 4 2002 4495