评估β-氨基酸作为哈ajos-帕里什-埃德尔-绍尔-维歇特反应的对映选择性有机催化剂。

Evaluating beta-amino acids as enantioselective organocatalysts of the Hajos-Parrish-Eder-Sauer-Wiechert reaction.

作者信息

Davies Stephen G, Russell Angela J, Sheppard Ruth L, Smith Andrew D, Thomson James E

机构信息

Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Oxford, UK.

出版信息

Org Biomol Chem. 2007 Oct 7;5(19):3190-200. doi: 10.1039/b711171a. Epub 2007 Aug 29.

DOI:10.1039/b711171a

PMID:17878978

Abstract

A systematic study of the effect of substitution within the beta-amino acid framework indicates that both beta(2)- and beta(3)-amino acids catalyse the Hajos-Parrish-Eder-Sauer-Wiechert reaction with poor to reasonable levels of enantioselectivity. These results led to the evaluation of the conformationally constrained beta-amino acid (1R,2S)-cispentacin, which catalyses the Hajos-Parrish-Eder-Sauer-Wiechert reaction with comparable or higher levels of enantioselectivity to L-proline.

摘要

对β-氨基酸框架内取代作用影响的系统研究表明，β(2)-和β(3)-氨基酸均能催化哈约什-帕里什-埃德尔-绍尔-维歇特反应，对映选择性水平从低到中等。这些结果促使人们对构象受限的β-氨基酸(1R,2S)-顺式喷他辛进行评估，它催化哈约什-帕里什-埃德尔-绍尔-维歇特反应时，对映选择性水平与L-脯氨酸相当或更高。