Regio- and stereoselective ring opening of 2,3-epoxyalcohols with diethylaluminium azide
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.
Bentley, Stuart; Goosen, Andre; Laue, Hugh A. H., Journal of Chemical Research, Miniprint, 1991, p. 1566 - 1590
作者:Bentley, Stuart、Goosen, Andre、Laue, Hugh A. H.、Taljaard, Benjamin
DOI:——
日期:——
Regio- and stereoselective ring opening of 2,3-epoxyalcohols with diethylaluminium azide
作者:Fabio Benedetti、Federico Berti、Stefano Norbedo
DOI:10.1016/s0040-4039(98)01733-x
日期:1998.10
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.