Asymmetric hydrogenation of imines catalysed by carboxylato(diphosphine)iridium(III) complexes

Tetrahedron Asymmetry

Volumn 7, Issue 11, 1996, Pages 3059-3062

  Sablong, Rafaël ^a   Osborn, John A ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

IRIDIUM COMPLEX; METAL COMPLEX;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030575819     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00397-7     Document Type: Article

References (32)

1. 1. Stinson, S.C. Chem. Eng. News, 1992, Sept.28, 46-63.
2. 2. For compilations, see: a) Noyori, R. Asymmetric Catalysis in Organic Synhtesis; Wiley: New York, 1994.
3. b) Kagan, H. B. In Comprehensive Organometallic Chemistry; Pergamon Press: Oxford, 1982, 8, pp 463-498.
4. c) Bosnich, B. Asymmetric Catalysis, Martinus Nijhoff: Dordrecht, 1986.
5. d) Noyori, R. Chem. Tech ., 1992, June, 360-372.
6. e) Noyori, R.; Chem. Soc. Rev., 1989, 18, 187.
7. e) Brown, J. M. Chem. Soc. Rev., 1993, 22, 25-41.
8. 3. a) Bakos, J.; Toth, I.; Heil B.; Szalontai, G.; Parkanyi L.; Fulop, V.J. Organomet. Chem., 1989, 370, 263-276.
9. b) Bakos, J.; Orosz, A.; Heil, B.; Laghmari, M.; Lhoste P.; Sinou, D. J. Chem. Soc., Chem. Commun., 1991, 1684-1685.
10. c) Amrani, Y.; Lecomte, L.; Sinou, D.; Bakos, J.; Toth I.; Heil, B. Organometallics, 1989, 8, 542-547.
11. d) Kang, G.-J.; Cullen, W.R.; Fryzuk, M.D.; James, B.R.; Kutney, J.P. J. Chem. Soc., Chem. Commun., 1988, 1466-1467.
12. e) Cullen, W.R.; Fryzuk, M.D.; James, B.R.; Kutney, J.P.; Kang, G.-J.; Herb, G.; Thorburn, I.S.; Spogliarich, R. J. Mol. Catal., 1990, 62, 243-253.
13. f) Bekalski, A.G.; Cullen, W.R.; Fryzuk, M.D.; James, B.R.; Kang, G.-J.; Rettig, S.J. Inorg. Chem, 1991, 30, 5002-5008.
14. g) Burk, M.J.; Feaster, J.E. J. Am. Chem. Soc., 1992, 114, 6266-6267.
15. h) Lensink C.; de Vries, J.G. Tetrahedron: Asymm., 1992, 3, 235-238.
16. 4. a) Spindler, F.; Pugin, B.; Blaser, H.-U. Angew. Chem. Int. Ed. Engl., 1990, 29, 558-559.
17. b) Morimoto, T.; Nakajima, N.; Achiwa, K. Synlett, 1995, 748-750.
18. c) Morimoto, T.; Achiwa, K. Tetrahedron: Asymm., 1995, 6, 2661-2664.
19. d) Sablong, R.; Osborn, J.A. Tetrahedron: Lett., 1996, 37, 4937-4940.
20. 5. Chan Y.P.N.C.; Osborn, J.A. J. Am. Chem. Soc., 1990, 112, 9400-9401.
21. 6. a) Kobayashi, K.; Okamoto, T.; Oida, T.; Tarimato, S. Chem. Lett., 1986, 2031-2034.
22. b) Willoughby, C.A.; Buchwald, S.L. J. Am. Chem. Soc., 1992, 114, 8652-8665.
23. c) Willoughby, C.A.; Buchwald S.L. J. Org. Chem. 1993, 58, 7627.
24. d) Verdaguer X.; Lange U.E.W.; Reding M.T.; Buchwald S.L. J. Am. Chem. Soc., 1996, 118, 6784.
25. e) Oppolzer W.; Wills M.; Starkemann C.; Bernadinelli G. Tetrahedron Lett., 1990, 31, 4117.
26. 7. The diphosphine structures are given below: (formula presented)
27. 1H}: -4.2 and -17.1 (AX, J = 31, 35%), -14.5 and -19.9 (AX, J = 26, 65%).
28. 9. Ogata, Y.; Takeushi, K.J. J. Org. Chem., 1970, 35, 1642-1645.
29. 10. a) Moser, H.; Rihs, G.; Sauter, H. Z. Naturforsch., 1982, 37b, 451-462.
30. b) U.S. Pats. 3 937 730 and 4 022 611 (1972) to Ciba-Geigy Ltd.
31. 11. Chadosh, D.; Crabtree, R.; Felkin, H.; Morehouse, S.; Morris, G. Inorg. Chem., 1982, 21, 1307-1311.
32. 12. Chan, Y.P.N.C.; Osborn, J.A. unpublished results.