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Issue 5, 2009
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In search of enantioselective catalysts for the Henry reaction: are two metal centres better than one?

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Abstract

Catalysts for the asymmetric Henry reaction involving copper(II) complexes of the chiral Schiff bases N,N′-(1R,2R)-(−)-1,2-cyclohexylenebis(3-hydroxysalicylideneamine) (H21) and N,N′-(1R,2R)-(−)-1,2-cyclohexylenebis(3-ethoxysalicylideneamine) (H22), and H23, which is the reduced analogue of H21, have been studied. Whereas [Cu(1)] and [Cu(2)] give poor yields and enantioselectivity, [Cu(3)] produced moderate to high yields and enantioselectivities were optimal when reactions were carried out in toluene rather than a polar solvent. A significant finding is that both yield and enantioselectivity are enhanced when a second equivalent of Cu(OAc)2 is added to the catalyst. The single-crystal structures of [Cu(3)] and [Cu(1)(H2O)] are presented, and the host–guest interactions and molecular packing in the latter are compared with those in [Cu(2)(H2O)].

Graphical abstract: In search of enantioselective catalysts for the Henry reaction: are two metal centres better than one?

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Article information


Submitted
09 Dec 2008
Accepted
22 Jan 2009
First published
20 Feb 2009

New J. Chem., 2009,33, 1064-1069
Article type
Paper

In search of enantioselective catalysts for the Henry reaction: are two metal centres better than one?

E. C. Constable, G. Zhang, C. E. Housecroft, M. Neuburger, S. Schaffner and Wolf-D. Woggon, New J. Chem., 2009, 33, 1064
DOI: 10.1039/B821995H

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