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

Article abstract of DOI:10.1016/S0040-4039(98)01733-X

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.