Asymmetric Catalytic Reduction with Transition Metal Complexes. I. A Catalytic System of Rhodium(I) with (–) -2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenyl-phosphino)butane, a New Chiral Diphosphine

Journal of the American Chemical Society

Volumn 94, Issue 18, 1972, Pages 6429-6433

  Kagan, Henri B ^a   Dang, Tuan Phat ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947089148     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00773a028     Document Type: Article

References (38)

1. E. I. Klabunovski and E. S. Levitina, Russ. Chem. Rev., 39, 1035 (1970).
2. Y. Izumi, M. Imaida, F. Fukowa, and S. Akabori, Bull. Chem. Soc. Jap., 36, 155 (1963);
3. Y. Izumi, S. Tatsumi, N. Imaida, Y. Fukuda, and S. Akabori, Bull. Chem. Soc. Jap., 39, 361 (1966).
4. J. A. Osborn, F. J. Jardine, J. F. Young, and G. Wilkinson, J. Chem. Soc., 1711 (1966);
5. S. Montelatici, A. van der Ent, J. A. Osborn, and G. Wilkinson, J. Chem. Soc. A, 1954 (1968).
6. R. Stern, Y. Chevallier, and L. Sajus, C. R. Acad. Sci., Ser. C, 264, 1970 (1967).
7. J. E. Lyons, L. E. Rennick, and J. L. Burneister, Ind. Eng. Chem., Prod. Res. Dev., 9, 2 (1970).
8. J. F. Biellmann and M. J. Jung, J. Amer. Chem. Soc., 90, 1673 (1968).
9. A. S. Hussey and Y. Takeuchi, J. Amer. Chem. Soc., 91, 672 (1969);
10. J. Org. Chem., 35, 643 (1970).
11. W. S. Knowles and M. J. Sabacky, Chem. Commun., 1445 (1968);
12. W. S. Knowles, M. J. Sabacky, and B. D. Vineyard, Ann. N. Y. Acad. Sci., 172, 232 (1970).
13. L. Horner, H. Siegel, and H. Buthe, Angew. Chem. Int. Ed. Engl, 7, 941 (1968).
14. J. D. Morrison, R. E. Burnett, A. M. Agniar, C. J. Morrow, and C. Phillips, J. Amer. Chem. Soc., 93, 1301 (1971).
15. T. P. Dang and H. B. Kagan, unpublished results.
16. T. P. Dang and H. B. Kagan, Chem. Commun., 481 (1971); patents pending.
17. H. Brunner, Angew, Chem., Int. Ed. Engl., 10, 249 (1971).
18. K. Issleib and G. Thomas, Chem. Ber., 93, 803 (1960).
19. 17 (b) Y. Chevallier, Docteur-Ingénieur Thesis, Paris, 1970, reprint available from Technip editor (Paris).
20. W. S. Knowles, M. J. Sabacky, and B. D. Vineyard, Chem. Commun., 10 (1972).
21. Y. H. Suen, A. Horeau, and H. B. Kagan, Bull. Soc. Chim. Fr., 1454 (1965);
22. A. La Manna, V. Ghislandi, O. B. Hulbert, and O. M. Scopes, Farmaco, Ed. Sci., 22, 1037 (1967).
23. R. M. Herbst and D. Shemin, “Organic Syntheses,” Collect. Vol. II, Wiley, New York, N. Y., 1943, p 1.
24. H. B. Gillespie and H. R. Snyder in ref 19, p 489.
25. A. H. Cook, G. Harris, and I. Heilbron, J. Chem. Soc., 1060 (1948).
26. E. Rohstein, J. Chem. Soc., 1968 (1969).
27. H. D. Dakin, J. Biol. Chem., 82, 443 (1932).
28. See Yamada, et al., Table III, footnote b.
29. E. Erlenmeyer, Jr., and J. T. Halsey, Ann., 307, 138 (1899).
30. E. Erlenmeyer, Jr., and J. Kunlin, Ann., 316, 150 (1901).
31. G. R. Ramage and J. L. Simonsen, J. Chem. Soc., 532 (1935).
32. H. L. Wheeler and C. Hoffman, Amer. Chem. J., 45, 368 (1911).
33. L. Porri, A. Lionetti, G. Allegra, and A. Immirzi, Chem. Commun., 336 (1965).
34. G. Winkhaus and H. Singer, Chem. Ber., 3602 (1966).
35. G. Darzens and Sejourne, C. R. Acad. Sci., 154, 1615 (1912).
36. P. W. Feit, J. Med. Chem., 7, 14 (1964).
37. H. Carmack and C. J. Kelley, J. Org. Chem., 33, 2171 (1968).
38. K. Issleib and D. W. Muller, Chem. Ber., 92, 3175 (1959).