Polymer-supported organocatalysts: Asymmetric reduction of imines with trichlorosilane catalyzed by an amino acid-derived formamide anchored to a polymer

Malkov, A. V., Figlus, M. and Kocovsky, P. (2008) Polymer-supported organocatalysts: Asymmetric reduction of imines with trichlorosilane catalyzed by an amino acid-derived formamide anchored to a polymer. Journal of Organic Chemistry, 73(11), pp. 3985-3995. (doi: 10.1021/jo800094q)

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Abstract

Asymmetric reduction of ketimines 1a-e with trichlorosilane can be catalyzed by the N-methylvaline-derived Lewis basic formamide anchored to a polymeric support (5a and 5b) with good enantioselectivity (<= 82% ee) and low catalyst loading (typically 15 mol %) at room temperature. This protocol represents a considerable simplification of the isolation procedure and is particularly suitable for a parallel synthesis of chiral amines 2a-e. The polymer-supported catalysts retain full activity after a multiple use.

Item Type:Articles
Keywords:ALPHA,BETA-UNSATURATED ALDEHYDES AMINE AROMATIC KETIMINES Asymmetric reduction CATALYST CATALYSTS Chiral HIGHLY ENANTIOSELECTIVE HYDROGENATION Hydrosilylation IMINES IR-F-BINAPHANE KETONES METAL-FREE N-ARYL IMINES ORGANIC ACTIVATORS ORGANOCATALYSTS polymer-supported catalysts POLYMER-SUPPORTED ORGANOCATALYSTS REDUCTION ROOM-TEMPERATURE STEREOSELECTIVE REDUCTION TEMPERATURE Trichlorosilane
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Malkov, Dr Andrei and Figlus, Mr Marek and Kocovsky, Professor Pavel
Authors: Malkov, A. V., Figlus, M., and Kocovsky, P.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
ISSN:0022-3263

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