Diastereoselective addition of allylmetal compounds to imines derived from (S)-1-phenylethanamine

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 9, 1996, Pages 875-882

  Alvaro, Giuseppe ^a   Boga, Carla ^a   Savoia, Diego ^a   Umani Ronchi, Achille ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542606898     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960000875     Document Type: Article

References (49)

1. J. D. Morrison, Asymmetric Synthesis, Academic Press, New York, 1983;
2. D. J. Hart and D.-C. Ha, Chem. Rev., 1989, 89, 1447;
3. P. J. Cox and N. S. Simpkins, Tetrahedron: Asymmetry, 1991, 2, 1;
4. F. H. Van der Steen and G. Van Koten, Tetrahedron, 1991, 47, 7503;
5. J. d'Angelo, D. Desmaele, F. Dumas and A. Guingant, Tetrahedron: Asymmetry, 1992, 3, 459;
6. R. M. Williams and J. A. Hendrix, Chem. Rev., 1992, 92, 889.
7. (a) Hydrogenolysis: M. K. Anwer and A. F. Spatola, Synthesis, 1980, 929;
8. S. Ram and L. D. Spicer, Tetrahedron Lett., 1987, 28, 515;
9. (b) Selective hydrogenolysis of dibenzylic amines: P. Polniaszek and L. W. Dillard, Tetrahedron Lett., 1990, 31, 797;
10. G. Bringmann and J.-P. Geisler, Synthesis, 1989, 608;
11. G. Bringmann, G. Kunkel and T. Geuder, Synlett, 1990, 253;
12. G. Bringmann, J.-P. Geisler, G. Kunkel and L. Kinzinger, Liebigs Ann. Chem., 1990, 795;
13. S. G. Davies and O. Ichihara, Tetrahedron: Asymmetry, 1991, 2, 183;
14. K. Hattori and H. Yamamoto, Tetrahedron, 1994, 50, 2785;
15. 2O: F. X. Webster, J. G. Millar and R. M. Silverstein, Tetrahedron Lett., 1986, 27, 4941.
16. Y. Yamamoto, Acc. Chem. Res. 1987, 20, 243;
17. Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207.
18. Y. Yamamoto, T. Komatsu and K. Maruyama, J. Am. Chem. Soc., 1984, 106, 5031;
19. Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu and W. Ito, J. Am. Chem. Soc., 1986, 108, 7778.
20. Y. Yamamoto and W. Itoh, Tetrahedron, 1988, 44, 5415.
21. D. J. Hallet and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1995, 657.
22. W. Neumann, M. M. Rogic and T. J. Dunn, Tetrahedron Lett., 1991, 32, 5865.
23. Y. Yamamoto, T. Komatsu and K. Maruyama, J. Chem. Soc., Chem. Commun. 1985, 814.
24. K. J. Beresford, G. P. Howe and G. Procter, Tetrahedron Lett., 1992, 33, 3355.
25. P. Beuchet, N. Le Marrec and P. Mosset, Tetrahedron Lett., 1992, 5959.
26. Some results have been reported in preliminary form: A. Bocoum, C. Boga, D. Savoia and A. Umani-Ronchi, Tetrahedron Lett., 1991, 32, 1367.
27. (a) A. Bocoum, D. Savoia and A. Umani-Ronchi, J. Chem. Soc., Chem. Commun., 1993, 1542;
28. (b) T. Basile, A. Bocoum, D. Savoia and A. Umani-Ronchi, J. Org. Chem., 1994, 59, 7766.
29. T. Mukaiyama, T. Harada and S. Skoda, Chem. Lett., 1981, 1507.
30. H. Tanaka, T. Takahara, H. Dhimane and S. Torii, Tetrahedron Lett., 1989, 30, 4161.
31. J. G. Noltes and J. W. G. Van Den Hurk, J. Organomet. Chem., 1965, 3, 222.
32. J. Reinhold, R. Benedix, P. Birner and H. Henning, Inorg. Chim. Acta, 1979, 33, 209.
33. E. Wissing, E. Rijnberg, P. A. van der Schaaf, K. van Gorp, J. Boersma and G. van Koten, Organometallics, 1994, 13 2609; and previous papers in the series.
34. J. J. C. Gros and S. Bourcier, in Stereochemistry, ed. H. B. Kagan, Georg Thieme Publishers, Stuttgart, 1977, Vol. 4.
35. M. B. Eleveld, H. Hogeveen and E. P. Schudde, J. Org. Chem., 1986, 51, 3635.
36. A. Bernardi, A. M. Capelli, A. Comotti, C. Gennari, M. Gardner, J. M. Goodman and I. Paterson, Tetrahedron, 1991, 47, 3471.
37. F. H. van der Steen, H. Kleijn, A. L. Spek and G. van Koten, J. Org. Chem., 1991, 56, 5868.
38. W. R. Roush, in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon Press, London and New York, 1991, vol. 2, p. 1.
39. E. J. Corey, C. P. Decicco and R. C. Newbold, Tetrahedron Lett., 1991, 32, 5287.
40. G. B. Jones and B. J. Chapman, Synthesis, 1995, 475.
41. (a) F. Bernardi, A. Bongini, G. Cainelli, M. A Robb and G. Suzzi Valli, J. Org. Chem., 1993, 58, 750;
42. (b) X. Wang and C. Lee, Tetrahedron Lett., 1993, 34, 6241;
43. (c) J. Maiz, A. Arrieta, X. Lopez, J. M. Ugalde and F. Cossio, Tetrahedron Lett., 1993, 34, 6111.
44. H. E. Smith, S. L. Cook and M. E. Warren, Jr., J. Org. Chem., 1964, 29, 2265.
45. F. Nerdel, K. Becker and G. Kresze, Chem. Ber., 1956, 89, 2862.
46. A. P. Terent'ev and V. M. Potapov, J. Gen. Chem. USSR (Engl. Transl.), 1958, 28, 1220.
47. K. Hattori and H. Yamamoto, Tetrahedron, 1993, 49, 1749.
48. H. Brunner, B. Reiter and G. Riepl, Chem. Ber., 1984, 117, 1330.
49. G. W. Kramer and H. C. Brown, J. Organomet. Chem., 1977, 132, 9.