Enantioselective synthesis of optically active homoallylamines by nucleophilic addition of chirally modified allylboranes to N-silylimines

Abstract

Enantioselectivity in the allylboration of N-silylimines with a variety of chirally modified allylboron reagents has been examined. Optically active N-sulfonylamino alcohols (16, 17 and 19) derived from D-camphor and norephedrine were found to be efficient chiral ligands for the allylboration reagent. These reagents smoothly reacted with N-silylimines to give the corresponding homoallylic amines in a high level of enantioselectivity up to 96% ee.

References

1. Reviews on allyl organometallics: (a) Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207; (b) W. R. Roush, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and C. F. Heathcock, Pergamon, Oxford, 1991, vol. 2, ch. 1.1For leading references on asymmetric allylboration of aldehydes: (c) R. W. Hoffmann and T. Herold, Chem. Ber., 1981, 114, 375; (d) T. Herold, U. Schrott and R. W. Hoffmann, Chem. Ber., 1981, 114, 359; (e) H. C. Brown and P. K. Jadhav, J. Org. Chem., 1984, 49, 4089; (f) U. S. Racherla and H. C. Brown, J. Org. Chem., 1991, 56, 401; (g) W. R. Roush, A. E. Walts and L. K. Hoong, J. Am. Chem. Soc., 1985, 107, 8186; (h) W. R. Roush, L. K. Hoong, M. A. J. Palmer and J. C. Park, J. Org. Chem., 1990, 55, 4109; (i) M. T. Reetz and T. Zierke, Chem. Ind., 1988, 663; (j) R. P. Short and S. Masamune, J. Am. Chem. Soc., 1989, 111, 1892; (k) E. J. Corey, C.-M. Yu and S. S. Kim, J. Am. Chem. Soc., 1989, 111, 5495.
2. H. C. Brown and P. V. Ramachandran, Pure Appl. Chem., 1991, 63, 307.
3. H. Moser, G. Rihs and H. Santer, Z. Naturforsch., Teil B, 1982, 37, 451; J. K. Whitesell, Chem. Rev., 1989, 89, 1581; J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995.
4. E. F. Kleinman and R. A. Volkmann, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and C. H. Heathcock, Pergamon, Oxford, 1991, vol. 2, ch. 4.3.
5. For a review on the asymmetric addition of nucleophiles to the C=N double bond, see: E. Denmark and O. J.-C. Nicaise, Chem. Commun., 1996, 999; D. Enders and U. Reinhold, Tetrahedron: Asymmetry, 1997, 8, 1895.
6. H. Nakamura, K. Nakamura and Y. Yamamoto, J. Am. Chem. Soc., 1998, 120, 4242.
7. M. Nakamura, A. Hirai and E. Nakamura, J. Am. Chem. Soc., 1996, 118, 8489.
8. I. Chataigner, F. Zammattio, J. Lebreton and J. Villiéras, Synlett, 1998, 275.
9. K. Watanabe, K. Ito and S. Itsuno, Tetrahedron: Asymmetry, 1995, 6, 1531; S. Itsuno, K. Watanabe, K. Ito, A. A. El-Shehawy and A. A. Sarhan, Angew. Chem., Int. Ed. Engl., 1997, 36, 109.
10. K. Watanabe, S. Kuroda, A. Yokoi, K. Ito and S. Itsuno, J. Organomet. Chem., 1999, 581, 103.
11. J. Sisko and S. Weinreb, J. Org. Chem., 1990, 55, 393.
12. G. Andersson, D. Guijarro and D. Tanner, J. Org. Chem., 1997, 62, 7364.
13. K. Soai, T. Hatanaka and T. Miyazawa, J. Chem. Soc., Chem. Commun., 1992, 1097.
14. H. C. Brown and P. K. Jadhav, J. Am. Chem. Soc., 1983, 105, 2092; P. K. Jadhav, K. S. Bhat, T. Perumal and H. C. Brown, J. Org. Chem., 1986, 51, 432.
15. G.-M. Chen, P. V. Ramachandran and H. C. Brown, Angew. Chem., Int. Ed., 1999, 38, 825.
16. W. R. Roush, A. D. Palkowitz and K. Ando, J. Am. Chem. Soc., 1990, 112, 6348; W. R. Roush, K. Ando, D. B. Powers, A. D. Palkowitz and R. H. Halterman, J. Am. Chem. Soc., 1990, 112, 6339.
17. G. Cainelli, D. Giacomini, P. Galletti and A. Gaiba, Synlett, 1996, 657.
18. D. J. Hart, K. Kanai, D. G. Thomas and T. K. Yang, J. Org. Chem., 1983, 48, 289.
19. T. Basile, A. Bocoum, D. Savoia and A. Umani-Ronchi, J. Org. Chem., 1994, 59, 7766.