Tetrahedron Letters p. 7971 - 7974 (1998)
Update date:2022-08-03
Topics:
Benedetti, Fabio
Berti, Federico
Norbedo, Stefano
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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Doi:10.1021/jm00079a024
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