The synthetic versatility of acyloxyborohydrides

被引：31

作者：

Gribble, Gordon W. ^{[1
]}

机构：

[1] Dartmouth Coll, Dept Chem, Hanover, NH 03755 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2006年 / 10卷 / 05期

关键词：

D O I：

10.1021/op060107s

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Acyloxyborohydrides are unsurpassed in their versatility as reagents in organic synthesis. In addition to their superior ability in effecting reductive amination of aldehydes and ketones, acyloxyborohydrides can reduce nitrogen heterocycles (indoles, quinolines, isoquinolines), imines, enamines, oximes, amides, nitriles, benzylic alcohols, aryl ketones, aldehydes ( but not ketones), acetals, beta-hydroxy ketones, and other substrates. The ability to control chemoselectivity, regioselectivity, and stereoselectivity by adjusting the carboxylic acid, borohydride reagent, stoichiometry, and temperature has no parallel in the repertoire of the organic chemist.

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页码：1062 / 1075

页数：14

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