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

被引：58

作者：

Benedetti, F ^{[1
]}

Berti, F ^{[1
]}

Norbedo, S ^{[1
]}

机构：

[1] Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 43期

关键词：

aluminium and compounds; azides; epoxides; isosteres;

D O I：

10.1016/S0040-4039(98)01733-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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, (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：7971 / 7974

页数：4

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