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Issue 5, 2013
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l-Pipecolinic acid derived Lewis base organocatalyst for asymmetric reduction of N-aryl imines by trichlorosilane: effects of the side amide group on catalytic performances

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Abstract

A series of N-formamides derived from pipecolinic acid have been synthesized and tested as Lewis base catalysts for the enantioselective reduction of N-aryl imines by trichlorosilane. Through the investigation of the structure–efficacy relationship between the side amide group and catalytic performance, several highly effective catalysts were discovered. In particular, arylamido-type catalyst 5i and non-arylamido-type catalyst 6c exhibited high reactivity and enantioselectivity, furnishing the reduction of a wide variety of N-aryl imines with high isolated yields (up to 98%) and ee values (up to 96%) under mild conditions. Moreover, these two catalysts complement each other in terms of their tolerances to nonaromatic ketimines and non-methyl ketimines.

Graphical abstract: l-Pipecolinic acid derived Lewis base organocatalyst for asymmetric reduction of N-aryl imines by trichlorosilane: effects of the side amide group on catalytic performances

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Publication details

The article was received on 08 Sep 2012, accepted on 11 Nov 2012 and first published on 12 Nov 2012


Article type: Paper
DOI: 10.1039/C2OB26772A
Org. Biomol. Chem., 2013,11, 787-797

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    L-Pipecolinic acid derived Lewis base organocatalyst for asymmetric reduction of N-aryl imines by trichlorosilane: effects of the side amide group on catalytic performances

    Z. Wang, C. Wang, L. Zhou and J. Sun, Org. Biomol. Chem., 2013, 11, 787
    DOI: 10.1039/C2OB26772A

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