Enantioselective photochemical synthesis of a β-lactam via the solid state ionic chiral auxiliary method

被引：1

作者：

Scheffer, J.R. ^{[1
]}

Wang, K. ^{[1
]}

机构：

[1] Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver V6T 1Z1, Canada

来源：

Synthesis | 2001年 / 08期

关键词：

Ammonia - Carboxylic acids - Crystals - Photolysis;

D O I：

10.1055/s-2001-15056

中图分类号：

学科分类号：

摘要：

Photolysis of crystals of a carboxylic acid-containing N,N-dialkylarylglyoxylamide to which an optically pure ammonium ion (the ionic chiral auxiliary) has been attached through a salt bridge leads to a 91% isolated yield of a β-lactam in greater than 99% enantiomeric excess. Suspension of the crystals in hexane allows the photoreaction to be carried out on a 500 mg scale, thus demonstrating the synthetic utility of the solid state ionic chiral auxiliary approach to asymmetric synthesis.

引用

页码：1253 / 1257

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