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迈向完美的催化不对称合成:亲电试剂和亲核试剂的双重活化

Towards perfect catalytic asymmetric synthesis: dual activation of the electrophile and the nucleophile.

作者信息

Ma Jun-An, Cahard Dominique

机构信息

UMR 6014 CNRS de l'IRCOF, Université de Rouen, 1 Rue Tesnière, 76 821 Mont Saint Aignan Cedex, France.

出版信息

Angew Chem Int Ed Engl. 2004 Sep 6;43(35):4566-83. doi: 10.1002/anie.200300635.

Abstract

The design and development of new high-performance catalysts for applications in asymmetric catalytic reactions is of ongoing interest in organic chemistry. The combination of a Lewis acid and a Lewis base working in concert is now considered state of the art in stereoselective syntheses. The synergistic activation by two or more reactive centers allows high reaction rates and excellent transfer of stereochemical information. Despite the self-quenching reaction between Lewis acids and Lewis bases that might lead to an inactive catalyst, considerable effort has been directed towards the development of the dual-activation concept. The ultimate goal is to mimic nature by the discovery of catalytic systems analogous to enzymatic processes that involve metal-ion cocatalysts. With this aim, the dual activation concept greatly broadens the range of artificial catalysts. The most efficient catalytic systems are reviewed, and the mechanisms of action are discussed.

摘要

设计和开发用于不对称催化反应的新型高性能催化剂一直是有机化学领域的研究热点。目前,协同作用的路易斯酸和路易斯碱组合被认为是立体选择性合成的先进技术。两个或多个反应中心的协同活化能够实现高反应速率和出色的立体化学信息传递。尽管路易斯酸和路易斯碱之间的自猝灭反应可能导致催化剂失活,但人们仍在大力研发双活化概念。最终目标是通过发现类似于涉及金属离子共催化剂的酶促过程的催化体系来模拟自然。出于这一目的,双活化概念极大地拓宽了人工催化剂的范围。本文综述了最有效的催化体系,并讨论了其作用机制。

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