Literature DB >> 24939397

Rhodium-catalyzed asymmetric hydrogenation of unprotected NH imines assisted by a thiourea.

Qingyang Zhao1, Jialin Wen, Renchang Tan, Kexuan Huang, Pedro Metola, Rui Wang, Eric V Anslyn, Xumu Zhang.   

Abstract

Asymmetric hydrogenation of unprotected NH imines catalyzed by rhodium/bis(phosphine)-thiourea provided chiral amines with up to 97% yield and 95% ee. (1)H NMR studies, coupled with control experiments, implied that catalytic chloride-bound intermediates were involved in the mechanism through a dual hydrogen-bonding interaction. Deuteration experiments proved that the hydrogenation proceeded through a pathway consistent with an imine.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; hydrogenation; ion pairs; reaction mechanisms; rhodium

Mesh：

Substances：

Year:  2014        PMID： 24939397      PMCID： PMC5989712          DOI： 10.1002/anie.201404570

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  47 in total

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Review 8.  Chiral Thioureas-Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry.

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