Tetrahedron letters

Regio-and stereoselective ring opening of 2, 3-epoxyalcohols with diethylaluminium azide

F Benedetti, F Berti, S Norbedo

Index: Benedetti, Fabio; Berti, Federico; Norbedo, Stefano Tetrahedron Letters, 1998 , vol. 39, # 43 p. 7971 - 7974

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Citation Number: 57

Abstract

2, 3-Epoxyalcohols react with diethylaluminium azide under mild conditions to give 3-azido- 1, 2-diols resulting from the regio-and stereoselective attack of the nucleophile at the epoxide C-3. The high regioselectivity (> 25: 1) observed with both cis and trans substituted epoxides is not affected by bulky substituents at C-3. The method has been successfully applied also to the synthesis of diaminodiol dipeptide isosteres.

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