Dendron-anchored organocatalysts: the asymmetric reduction of imines with trichlorosilane, catalysed by an amino acid-derived formamide appended to a dendron

Figlus, M., Caldwell, S.T. , Walas, D., Yesilbag, G., Cooke, G. , Kocovsky, P., Malkov, A.V. and Sanyal, A. (2010) Dendron-anchored organocatalysts: the asymmetric reduction of imines with trichlorosilane, catalysed by an amino acid-derived formamide appended to a dendron. Organic and Biomolecular Chemistry, 8(1), pp. 137-141. (doi:10.1039/b916601g)

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Abstract

Asymmetric reduction of ketimines 1a-f with trichlorosilane can be catalysed by the Lewis-basic N-methylvaline-derived formamide anchored to a soluble dendron (11c) with good enantioselectivity (<= 94% ee) and low catalyst loading (typically 5 mol%) at room temperature in toluene. This protocol represents an improvement and simplification of the isolation procedure and recovery of the catalyst.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Caldwell, Dr Stuart and Kocovsky, Professor Pavel and Figlus, Mr Marek and Cooke, Professor Graeme
Authors: Figlus, M., Caldwell, S.T., Walas, D., Yesilbag, G., Cooke, G., Kocovsky, P., Malkov, A.V., and Sanyal, A.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic and Biomolecular Chemistry
ISSN:1477-0520
Published Online:27 October 2009

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
438151A physical and organic chemistry approach to the design and study of Redox Tuneable Hydrogen Bonded ComplexesGraeme CookeEngineering & Physical Sciences Research Council (EPSRC)EP/E018211/1Chemistry
370221New organocatalysts from amino acids exploitation of Chiral Relay and Aromatic Interactions in Asymmetric CatalysisAndrei MalkovEngineering & Physical Sciences Research Council (EPSRC)GR/S87294/01Chemistry