Evidence for the importance of conformational equilibria in Rh-diphosphine complexes for the enantioselection in Rh-catalyzed asymmetric hydrogenation

Tetrahedron Letters

Volumn 46, Issue 16, 2005, Pages 2879-2882

  Tsuruta, Hideyuki ^a   Imamoto, Tsuneo ^a   Yamaguchi, Kentaro ^a   Gridnev, Ilya D ^b  

^a CHIBA UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

Asymmetric hydrogenation; Chiral diphosphines; Chiral rhodium complexes; Sense of enantioselection

Indexed keywords

1,2 BIS[(2 METHYLPHENYL)PHENYLPHOSPHINO]ETHANE; ALKADIENE; AMINO ACID; ETHANE; PHOSPHINE DERIVATIVE; RHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHELATION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATION; ENANTIOSELECTIVITY; HYDROGENATION; REACTION ANALYSIS; X RAY ANALYSIS;

EID: 15944403176     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.115     Document Type: Article

References (36)

1. For representative reviews, see: W.S. Knowles Angew. Chem., Int. Ed. 41 2002 1998
2. R. Noyori Angew. Chem., Int. Ed. 41 2002 2008
3. T. Ohkuma, M. Kitamura, and R. Noyori 2nd ed. I. Ojima Catalytic Asymmetric Synthesis 2000 VCH New York 1 110
4. R. Noyori, M. Kitamura, and T. Ohkuma Proc. Natl. Acad. Sci. U.S.A. 101 2004 5356
5. For recent review, see: W. Tang, and X. Zhang Chem. Rev. 103 2003 3029
6. J. Halpern, D.P. Riley, A.S.C. Chan, and J.J. Pluth J. Am. Chem. Soc. 99 1977 8055
7. J.M. Brown, and P.A. Chaloner Tetrahedron Lett. 1978 1877
8. J.M. Brown, and P.A. Chaloner J. Am. Chem. Soc. 102 1980 3040
9. A.S.C. Chan, J.J. Pluth, and J. Halpern J. Am. Chem. Soc. 102 1980 5952
10. C.R. Landis, and J. Halpern J. Am. Chem. Soc. 109 1987 1746
11. I.D. Gridnev, N. Higashi, K. Asakura, and T. Imamoto J. Am. Chem. Soc. 122 2000 7183
12. R. Giernoth, H. Heinrich, N.J. Adams, R.J. Deeth, J. Bargon, and J.M. Brown J. Am. Chem. Soc. 122 2000 12381
13. I.D. Gridnev, M. Yasutake, N. Higashi, and T. Imamoto J. Am. Chem. Soc. 123 2001 5268
14. I.D. Gridnev, Y. Yamanoi, N. Higashi, H. Tsuruta, M. Yasutake, and T. Imamoto Adv. Synth. Catal. 343 2001 118
15. I.D. Gridnev, N. Higashi, and T. Imamoto J. Am. Chem. Soc. 123 2001 4631
16. I.D. Gridnev, and T. Imamoto Acc. Chem. Res. 37 2004 633
17. C.R. Landis, P. Hilfenhaus, and S. Feldgus J. Am. Chem. Soc. 121 1999 8741
18. C.R. Landis, and S. Feldgus Angew. Chem. Int., Ed. 39 2000 2863
19. S. Feldgus, and C.R. Landis J. Am. Chem. Soc. 122 2000 12714
20. S. Feldgus, and C.R. Landis Organometallics 20 2001 2374
21. H.-J. Drexler, S. Zhang, A. Sun, A. Spannenberg, A. Arrleta, A. Preetz, and D. Heller Tetrahedron: Asymmetry 15 2004 2139
22. I.D. Gridnev, and T. Imamoto Acc. Chem. Res. 37 2004 633
23. H. Shimizu, T. Ishizaki, T. Fujiwara, and T. Saito Tetrahedron: Asymmetry 15 2004 2169
24. δ,λ-Rule: M.D. Fryzuk, and B. Bosnich J. Am. Chem. Soc. 100 1978 5491
25. O. Samuel, R. Couffignal, M. Lauer, S.Y. Zhang, and H.B. Kagan Nouv. J. Chem. 5 1981 15
26. H.B. Kagan G. Wilkinson F.G.A. Stone E.W. Abel Asymmetric Synthesis Using Organometallic Catalysis Vol. 8 1982 Pergamon Oxford 463 498
27. Quadrant rule: K.E. Koenig, M.J. Sabacky, G.L. Bachman, W.C. Christopfel, H.D. Barnstoff, R.B. Friedman, W.S. Knowles, B.R. Stults, B.D. Vineyard, and D. Weinkauff Ann. N.Y. Acad. Sci. 333 1980 16
28. W.S. Knowles Acc. Chem. Res. 16 1983 106
29. Twist of coordinated diene: E.P. Kyba, R.E. Davis, P.N. Juri, and K.R. Shirley Inorg. Chem. 20 1981 3616
30. T. Imamoto, J. Watanabe, Y. Wada, H. Masuda, H. Yamada, H. Tsuruta, S. Matsukawa, and K. Yamaguchi J. Am. Chem. Soc. 120 1998 1635
31. B.D. Vineyard, W.S. Knowles, G.L. Sabacky, G.L. Bachman, and D.J. Weinkauff J. Am. Chem. Soc. 99 1977 5946
32. J. Bakos, I. Tóth, B. Heil, G. Szalontai, L. Párká nyi, and V. Fülöp J. Organomet. Chem. 370 1989 263
33. Y. Wada, T. Imamoto, H. Tsuruta, K. Yamaguchi, and I.D. Gridnev Adv. Synth. Catal. 346 2004 777
34. 1 = 0.067. CCDC 233230
35. 1 = 0.066. CCDC 233231
36. Yoshikuni and Bailar, Jr. reported that asymmetric hydrogenation of acetamidoacrylic acid catalyzed by a rhodium complex of optically active bis[(o-methylphenyl)phenylphosphine]ethane afforded N-acetylalanine with 63.2% ee. However, the enantiomeric excess of the rhodium complex was not given in their paper T. Yoshikuni, and J.C. Bailar Jr. Inorg. Chem. 21 1982 2129