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轴手性胍作为不对称取代1,3 - 二羰基化合物亲电胺化反应的高活性和对映选择性催化剂。

Axially chiral guanidine as highly active and enantioselective catalyst for electrophilic amination of unsymmetrically substituted 1,3-dicarbonyl compounds.

作者信息

Terada Masahiro, Nakano Megumi, Ube Hitoshi

机构信息

Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.

出版信息

J Am Chem Soc. 2006 Dec 20;128(50):16044-5. doi: 10.1021/ja066808m.

DOI:10.1021/ja066808m
PMID:17165751
Abstract

A newly designed axially chiral guanidine is found to function as an effective platform for asymmetric induction at the alpha-carbon of unsymmetrically substituted 1,3-dicarbonyl compounds. Highly efficient and enantioselective electrophilic amination of various 1,3-dicarbonyl compounds with azodicarboxylate was successfully achieved using the present chiral guanidine catalyst, which provides efficient access to the construction of nitrogen-substituted quaternary stereocenters in an optically active form.

摘要

一种新设计的轴手性胍被发现可作为一个有效的平台,用于在不对称取代的1,3 - 二羰基化合物的α-碳上进行不对称诱导。使用目前的手性胍催化剂,成功实现了各种1,3 - 二羰基化合物与偶氮二甲酸酯的高效对映选择性亲电胺化反应,这为以光学活性形式构建氮取代的季碳立体中心提供了有效途径。

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