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

Marek Figlus; Stuart T. Caldwell; Dawid Walas; Gulen Yesilbag; Graeme Cooke; Pavel Kočovský; Andrei V. Malkov; Amitav Sanyal

doi:10.1039/B916601G

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Organic & Biomolecular Chemistry

Issue 1, 2010

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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

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

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

DOI: 10.1039/B916601G
Received 12 Aug 2009, Accepted 25 Sep 2009
First published on the web 27 Oct 2009

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Abstract
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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.

Abstract from Catalysts & Catalysed Reactions 2010

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General methods, and ¹H and ¹³C NMR spectra of the dendron-anchored catalysts 11a–c
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Marek Figlus
Stuart T. Caldwell
Dawid Walas
Gulen Yesilbag
Graeme Cooke
Pavel Kočovský
Andrei V. Malkov
Amitav Sanyal

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Organic & Biomolecular Chemistry

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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