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布朗斯特酸活化策略在过渡金属催化的 N-未保护亚胺、烯胺和 N-杂芳环化合物的不对称氢化中的应用。

Brønsted acid activation strategy in transition-metal catalyzed asymmetric hydrogenation of N-unprotected imines, enamines, and N-heteroaromatic compounds.

机构信息

Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, Liaoning 116023, China.

出版信息

Angew Chem Int Ed Engl. 2012 Jun 18;51(25):6060-72. doi: 10.1002/anie.201200963. Epub 2012 May 10.

Abstract

Asymmetric hydrogenation plays an important role in organic synthesis, but that of the challenging substrates such as N-unprotected imines, enamines, and N-heteroaromatic compounds (1H-indoles, 1H-pyrroles, pyridines, quinolines, and quinoxalines) has only received increased attention in the past three years. Considering the interaction modes of a Brønsted acid with a Lewis base, Brønsted acids may be used as the ideal activators of C=N bonds. This Minireview summarizes the recent advances in transition-metal-catalyzed, Brønsted acid activated asymmetric hydrogenation of these challenging substrates, thus offering a promising substrate activation strategy for transformations involving C=N bonds.

摘要

不对称氢化在有机合成中起着重要作用,但在过去三年中,人们才开始更多地关注 N-未保护的亚胺、烯胺和 N-杂芳族化合物(1H-吲哚、1H-吡咯、吡啶、喹啉和喹喔啉)等具有挑战性的底物的不对称氢化。考虑到布朗斯特酸与路易斯碱的相互作用模式,布朗斯特酸可用作 C=N 键的理想活化剂。本综述总结了近年来过渡金属催化、布朗斯特酸活化这些具有挑战性的底物的不对称氢化的最新进展,从而为涉及 C=N 键的转化提供了一种很有前途的底物活化策略。

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