脯氨酸介导的醛α-胺化反应中原位催化剂的改进

In situ catalyst improvement in the proline-mediated alpha-amination of aldehydes.

作者信息

Iwamura Hiroshi, Mathew Suju P, Blackmond Donna G

机构信息

Department of Chemistry, Imperial College, London SW7 2AZ, UK.

出版信息

J Am Chem Soc. 2004 Sep 29;126(38):11770-1. doi: 10.1021/ja046258x.

DOI:10.1021/ja046258x

PMID:15382893

Abstract

Kinetic investigations show that the proline-mediated alpha-amination of aldehydes exhibits autoinductive rate behavior and amplification of product enantiomeric excess. Further experiments highlight the role of product, offering suggestions for the design of catalysts of improved efficiency for such transformations. The unusual characteristics exhibited by these reactions implicate amino acid catalysis in rationalizations of the origin of biological homochirality.

摘要

动力学研究表明，脯氨酸介导的醛的α-胺化反应表现出自动诱导速率行为和产物对映体过量的放大。进一步的实验突出了产物的作用，为设计此类转化中效率更高的催化剂提供了建议。这些反应所表现出的异常特性表明，氨基酸催化作用可用于合理解释生物同手性的起源。