Issue 1, 2010
From the journal:

Organic & Biomolecular Chemistry

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

Marek Figlus,a   Stuart T. Caldwell,a   Dawid Walas,a   Gulen Yesilbag,b   Graeme Cooke,*a   Pavel Kočovský,*a   Andrei V. Malkov*ac  and  Amitav Sanyal*b  

* Corresponding authors

a WestCHEM, Department of Chemistry, Joseph Black Building, University of Glasgow, Glasgow, UK
E-mail: graemec@chem.gla.ac.uk, pavelk@chem.gla.ac.uk

b Department of Chemistry, Bogazici University, Bebek, Istanbul, Turkey
E-mail: amitav.sanyal@boun.edu.tr

c Department of Chemistry, Loughborough University, Loughborough, UK
E-mail: A.Malkov@lboro.ac.uk

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.

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

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Article information

DOI
https://doi.org/10.1039/B916601G
Article type
Paper
Submitted
12 Aug 2009
Accepted
25 Sep 2009
First published
27 Oct 2009

Org. Biomol. Chem., 2010,8, 137-141

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

M. Figlus, S. T. Caldwell, D. Walas, G. Yesilbag, G. Cooke, P. Kočovský, A. V. Malkov and A. Sanyal, Org. Biomol. Chem., 2010, 8, 137 DOI: 10.1039/B916601G

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