Issue 5, 2015

Quinine catalysed asymmetric Michael additions in a sustainable solvent

Abstract

Diethyl carbonate is shown to be a suitable, sustainable solvent in which to carry out quinine catalysed asymmetric Michael additions of malononitriles to enones. Both malonitrile and α-substituted malononitriles can be used as substrate and the results suggest that π–π stacking interactions between the (hetero)aromatic rings of the catalyst and substrates are important in determining the degree of asymmetric induction.

Graphical abstract: Quinine catalysed asymmetric Michael additions in a sustainable solvent

Supplementary files

Article information

Article type
Paper
Submitted
10 Oct 2014
Accepted
04 Dec 2014
First published
04 Dec 2014

RSC Adv., 2015,5, 3678-3685

Author version available

Quinine catalysed asymmetric Michael additions in a sustainable solvent

J. A. Castro-Osma, J. W. Comerford, S. Heath, O. Jones, M. Morcillo and M. North, RSC Adv., 2015, 5, 3678 DOI: 10.1039/C4RA12132E

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