Selective reductive cleavage of 2, 3-epoxybromides by the InCl 3–NaBH 4 reagent system

BC Ranu, S Banerjee, A Das

Index: Ranu, Brindaban C.; Banerjee, Subhash; Das, Arijit Tetrahedron Letters, 2004 , vol. 45, # 46 p. 8579 - 8581

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Citation Number: 24

Abstract

A combination of sodium borohydride and a catalytic amount of indium (III) chloride in acetonitrile reduces 2, 3-epoxybromides to the corresponding allylic alcohols in good yields involving reduction of the bromo moiety followed by selective C–O bond cleavage through a radical process. Several aromatic, cyclic and open-chain bromoepoxides successfully participated in this reaction.