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4-(二甲基氨基)吡啶“平面手性”衍生物的不对称催化作用

Asymmetric catalysis with "planar-chiral" derivatives of 4-(dimethylamino)pyridine.

作者信息

Fu Gregory C

机构信息

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

出版信息

Acc Chem Res. 2004 Aug;37(8):542-7. doi: 10.1021/ar030051b.

Abstract

Whereas chiral Lewis acid catalysis has been intensively investigated, chiral Lewis base (nucleophilic) catalysis has been comparatively neglected. We have developed "planar-chiral" derivatives of 4-(dimethylamino)pyridine (DMAP), a highly versatile nucleophilic catalyst, that are effective in a diverse array of processes, including the Staudinger synthesis of beta-lactams, the acylation of silyl ketene acetals, and the kinetic resolution of amines.

摘要

尽管手性路易斯酸催化已得到深入研究,但手性路易斯碱(亲核)催化却相对被忽视。我们已开发出4-(二甲氨基)吡啶(DMAP)的“平面手性”衍生物,DMAP是一种用途广泛的亲核催化剂,在多种反应过程中都很有效,包括β-内酰胺的施陶丁格合成、甲硅烷基烯酮缩醛的酰化反应以及胺的动力学拆分。

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