Regioselective Reductive Cleavage of Terminal Epoxideswith Polymer-supported ChloroaluminiumTetrahydroborate†

Abstract

Epoxides are reduced exclusively to the lesssubstituted alcohols with regenerable polyvinylpyridine-supportedchloroaluminium tetrahydroborate in high yields.

References

1. H. O. House, Modern Synthetic Reactions, W. A. Benzamin, California, 1972; F. A. Carey and R. J. Sandberg, Advanced Organic Chemistry, Part B, Plenum Press, New York, 1977.
2. (a) H. C. Brown and N. M. Yoon, J. Chem. Soc., Chem. Commun., 1968, 1519; (b) R. O. Hutchins, I. M. Taffer and W. Burgoynes, J. Org. Chem., 1981, 46, 5214 and references cited therein; (c) N. M. Yoon and K. E. Kim, J. Org. Chem., 1987, 52, 5364; (d) J. J. Eisch, Z. R. Liu and M. Singh, J. Org. Chem., 1992, 57, 1618; (e) B. C. Ranu and A. R. Das, J. Chem. Soc., Chem. Commun., 1990, 1334; (f) B. C. Ranu and A. R. Das, J. Chem. Soc., Perkin Trans., 1992, 1881; (g) A. C. Bonini, G. Righi and G. Sotgiu, J. Org. Chem., 1991, 56, 6206; (h) G. A. Epling and Q. Wang, J. Chem. Soc., Chem. Commun., 1992, 1133.
3. D. C. Sherrington and P. Hodge, Synthesis and Separations Using Functional Polymers, Wiley, New York, 1988.
4. H. W. Gibson and F. C. Bailey, J. Chem. Soc., Chem. Commun., 1977, 815; R. O. Hutchins, N. R. Natal and I. M. Taffer, J. Chem. Soc., Chem. Commun., 1978, 1088.
5. H. Firouzabadi, B. Tamami and N. Goudarzian, Synth. Commun., 1991, 21, 2275.
6. B. Tamami and N. Goudarzian, J. Chem. Soc., Chem. Commun., 1994, 1079.
7. B. Tamami and N. Goudarzian, Iranian J. Chem. Eng., in the press.
8. W. M. Olson and R. T. Sanderson, J. Inorg. Nucl. Chem., 1958, 7, 228.