A highly regio- and chemoselective synthesis of vicinal bromohydrins by ring opening of terminal epoxides with dibromoborane-dimethyl sulfide

被引：8

作者：

Roy, Chandra D. ^{[1
]}

Brown, Herbert C. ^{[1
]}

机构：

[1] Purdue Univ, Herbert C Brown Ctr Borane Res, Dept Chem, W Lafayette, IN 47907 USA

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2007年 / 692卷 / 07期

关键词：

epoxides; bromohydrin; dibromoborane-dimethyl sulfide; regioselectivity; chemoselectivity;

D O I：

10.1016/j.jorganchem.2006.11.032

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Dibromoborane-dimethyl sulfide (BHBr(2)-SMe(2)) displays high degrees of chemo- and regioselectivity during the brominative cleavage of the epoxy group into vicinal bromohydrins in the presence of alkene, alkyne, allene, ether, acetal and acetonide, besides its hydroborating ability. Several reducible functional groups, such as chloride, aldehyde, ketone, azide, ester, nitrile and tert-amino ester, have been successfully accommodated during the epoxide opening process. (c) 2006 Elsevier B.V. All rights reserved.

引用

页码：1608 / 1613

页数：6

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