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)

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 Cooke, Professor Graeme and Figlus, Mr Marek and Kocovsky, Professor Pavel
• 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

Project Code	Award No	Project Name	Principal Investigator	Funder's Name	Funder Ref	Lead Dept
43815	1	A physical and organic chemistry approach to the design and study of Redox Tuneable Hydrogen Bonded Complexes	Graeme Cooke	Engineering & Physical Sciences Research Council (EPSRC)	EP/E018211/1	Chemistry
37022	1	New organocatalysts from amino acids exploitation of Chiral Relay and Aromatic Interactions in Asymmetric Catalysis	Andrei Malkov	Engineering & Physical Sciences Research Council (EPSRC)	GR/S87294/01	Chemistry