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
收藏
页码：1253 / 1257
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