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 Cl<sub>3</sub>SiH (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