Soluble Polymer-Supported Organocatalysts: Asymmetric Reduction of Imines with Trichlorosilane Catalyzed by an Amino Acid Derived Formamide Anchored to a Soluble Polymer

Malkov, A. V., Figlus, M., Prestly, M. R., Rabani, G., Cooke, G. and Kocovsky, P. (2009) Soluble Polymer-Supported Organocatalysts: Asymmetric Reduction of Imines with Trichlorosilane Catalyzed by an Amino Acid Derived Formamide Anchored to a Soluble Polymer. Chemistry: A European Journal, 15(38), pp. 9651-9654. (doi:10.1002/chem.200901573)

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Publisher's URL: http://dx.doi.org/10.1002/chem.200901573

Abstract

A novel polymeric platform for catalyst immobilization has been developed, featuring inverted solubility pattern: soluble in a nonpolar and insoluble in a polar medium. Asymmetric reduction of imines with Cl3SiH (see scheme), catalyzed by chiral formamide anchored to this soluble polymer, proceeds under homogeneous conditions to give chiral amines in high yields and enantioselectivities (≤91 % ee).

Item Type:Articles
Keywords:ACID AMINATION AROMATIC KETIMINES Asymmetric reduction asymmetric synthesis DYNAMIC KINETIC RESOLUTION Enantioselective reduction IMINES N-ARYL IMINES ORGANIC ACTIVATORS Organocatalysis ORGANOCATALYSTS polymer-supported catalysts POLYMER-SUPPORTED ORGANOCATALYSTS RADICAL POLYMERIZATION RECOVERABLE CATALYSTS REDUCTION STEREOSELECTIVE REDUCTION TRANSFER HYDROGENATION Trichlorosilane.
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Malkov, Dr Andrei and Cooke, Professor Graeme and Rabani, Dr Gouher and Figlus, Mr Marek and Kocovsky, Professor Pavel
Authors: Malkov, A. V., Figlus, M., Prestly, M. R., Rabani, G., Cooke, G., and Kocovsky, P.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Chemistry: A European Journal
Journal Abbr.:Chem. Eur J.
Publisher:Wiley-VCH Verlag
ISSN:0947-6539
ISSN (Online):1521-3765
Published Online:26 August 2009

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
370221New organocatalysts from amino acids exploitation of Chiral Relay and Aromatic Interactions in Asymmetric CatalysisAndrei MalkovEngineering & Physical Sciences Research Council (EPSRC)GR/S87294/01Chemistry