Origin of diastereoselectivity in the addition of allylsilane to chiral acyclic mixed acetals

Abstract

Addition of allylsilane to chiral acyclic mixed acetals has been found to proceed via an S_N1 mechanism and a model has been proposed to explain the observed diastereoselectivity.

References

1. S. E. Denmark and N. G. Almstead, J. Am. Chem. Soc., 1991, 113, 8089; R. Silverman, C. Edington, J. D. Elliott and W. S. Johnson, J. Org. Chem., 1987, 52, 180; K. Maruoka and H. Yamamoto, Angew. Chem., Int. Ed. Engl., 1985, 24, 668; P. A. Bartlett, W. S. Johnson and J. D. Elliott, J. Am. Chem. Soc., 1983, 105, 2088; J. M. McNamara and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7371.
2. (a) A. Mekhalfia and I. E. Markó, Tetrahedron Lett., 1991, 32, 4779; (b) T. Mukaiyama, M. Ohshima and N. Miyoshi, Chem. Lett., 1987, 1121; (c) R. Imwinkelreid and D. Seebach, Angew. Chem., Int. Ed. Engl., 1985, 24, 765.
3. D. Sames, Y. Liu, L. DeYoung and R. Polt, J. Org. Chem., 1995, 60, 2153; T. Sammakia and R. S. Smith, J. Am. Chem. Soc., 1994, 116, 7915; I. Mori, K. Ishihara, L. A. Flippin, K. Nozaki, H. Yamamoto, P. A. Bartlett and C. H. Heathcock, J. Org. Chem., 1990, 55, 6107; S. E. Denmark and T. M. Willson, J. Am. Chem. Soc., 1989, 111, 3475; I. Mori, P. A. Bartlett and C. H. Heathcock, J. Am. Chem. Soc., 1987, 109, 7199.
4. R. W. Hoffmann, Chem. Rev., 1989, 89, 1841.
5. J. L. Broeker, R. W. Hoffmann and K. N. Houk, J. Am. Chem. Soc., 1991, 113, 5006.
6. S. Kiyooka, M. Shirouchi and Y. Kaneko, Tetrahedron Lett., 1993, 34, 1491.
7. N. Minowa and T. Mukaiyama, Bull. Chem. Soc. Jpn., 1987, 60, 3697.
8. M. E. Jung and M. A. Lyster, J. Org. Chem., 1977, 42, 3761.
9. G. Frenking, K. F. Köhler and M. T. Reetz, Tetrahedron, 1991, 47, 9005.
10. E. P. Lodge and C. H. Heathcock, J. Am. Chem. Soc., 1987, 109, 3353.
11. E. J. Corey, R. K. Bakshi and S. Shibata, J. Am. Chem. Soc., 1987, 109, 5551; H. Takahashi, T. Kawakita, M. Ohno, M. Yoshioka and S. Kobayashi, Tetrahedron, 1992, 48, 5691.
12. S. S. Wong and M. N. Paddon-Row, J. Chem. Soc., Chem. Commun., 1991, 327 Also see ref. 11.
13. N. T. Anh and O. Eisenstein, Nouv. J. Chim., 1977, 1, 62.
14. (a) S. Berger, B. W. K. Diehl and H. Künzer, Chem. Ber., 1987, 120, 1059; (b) W. J. Hehre and L. Salem, J. Chem. Soc., Chem. Commun., 1973, 754; (c) L. Radom, J. A. Pople and P. v. R. Schleyer, J. Am. Chem. Soc., 1972, 94, 5935.
15. W. M. Schubert, R. B. Murphy and J. Robins, J. Org. Chem., 1970, 35, 951; V. J. Shiner Jr. and J. S. Humphrey Jr., J. Am. Chem. Soc., 1963, 85, 2416.
16. R. J. Linderman and T. V. Anklekar, J. Org. Chem., 1992, 57, 5078.