Quinine catalysed asymmetric Michael additions in a sustainable solvent

José A. Castro-Osma; James W. Comerford; Samantha Heath; Oliver Jones; Maria Morcillo; Michael North

doi:10.1039/c4ra12132e

Quinine catalysed asymmetric Michael additions in a sustainable solvent

José A. Castro-Osma, James W. Comerford, Samantha Heath, Oliver Jones, Maria Morcillo, Michael North^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	3678-3685
Number of pages	8
Journal	RSC Advances
Volume	2015
Issue number	5
DOIs	https://doi.org/10.1039/c4ra12132e
Publication status	Published - 4 Dec 2014

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AU - Castro-Osma, José A.

AU - Comerford, James W.

AU - Heath, Samantha

AU - Jones, Oliver

AU - Morcillo, Maria

AU - North, Michael

PY - 2014/12/4

Y1 - 2014/12/4

N2 - 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.

AB - 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.

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Quinine catalysed asymmetric Michael additions in a sustainable solvent

Abstract

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