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Issue 71, 2014
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Probing the evolution of an Ar-BINMOL-derived salen–Co(iii) complex for asymmetric Henry reactions of aromatic aldehydes: salan–Cu(ii) versus salen–Co(iii) catalysis

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Abstract

A new type of chiral salen–Co catalyst that features aromatic π-walls and an active Co(III) center has been developed for enantioselective Henry/nitroaldol reactions on the basis of salen–Cu catalysis. The asymmetric Henry reaction of aromatic aldehydes and nitromethane catalyzed by an Ar-BINMOL-derived salen–Co(III) complex was achieved with high yields (up to 93%) and excellent enantioselectivities (up to 98% ee). And more interestingly, it was supposed that either salan–Cu(II) or salen–Co(III) complex-catalyzed Henry reaction was an ideal model reaction for providing direct evidence of noncovalent interaction due to the distinguishable ortho-substituted aromatic aldehydes from meta- or para-substituted benzaldehydes in terms of enantioselectivities and yields.

Graphical abstract: Probing the evolution of an Ar-BINMOL-derived salen–Co(iii) complex for asymmetric Henry reactions of aromatic aldehydes: salan–Cu(ii) versus salen–Co(iii) catalysis

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Supplementary files

Article information


Submitted
21 Jun 2014
Accepted
12 Aug 2014
First published
14 Aug 2014

RSC Adv., 2014,4, 37859-37867
Article type
Paper

Probing the evolution of an Ar-BINMOL-derived salen–Co(III) complex for asymmetric Henry reactions of aromatic aldehydes: salan–Cu(II) versus salen–Co(III) catalysis

Y. Wei, K. Yang, F. Li, Z. Zheng, Z. Xu and L. Xu, RSC Adv., 2014, 4, 37859
DOI: 10.1039/C4RA06056C

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