Regio- and stereoselective ring opening of 2,3-epoxyalcohols with diethylaluminium azide
1998; Elsevier BV; Volume: 39; Issue: 43 Linguagem: Inglês
10.1016/s0040-4039(98)01733-x
ISSN1873-3581
AutoresFabio Benedetti, Federico Berti, Stefano Norbedo,
Tópico(s)Chemical Synthesis and Analysis
Resumo2,3-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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