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

Figlus, M., Caldwell, S.T. ORCID: https://orcid.org/0000-0003-1604-3462, Walas, D., Yesilbag, G., Cooke, G. ORCID: https://orcid.org/0000-0003-0890-5720, 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.

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Funder and Project Information

1

A physical and organic chemistry approach to the design and study of Redox Tuneable Hydrogen Bonded Complexes

Graeme Cooke

EP/E018211/1

Chemistry

1

New organocatalysts from amino acids exploitation of Chiral Relay and Aromatic Interactions in Asymmetric Catalysis

Andrei Malkov

GR/S87294/01

Chemistry

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