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Issue 13, 2016
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Deracemizing organocatalyzed Michael addition reactions of 2-(arylthio)cyclobutanones with β-nitrostyrenes

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Abstract

Organocatalyzed Michael addition reactions of 2-(arylthio)cyclobutanones with trans-β-nitrostyrenes have been carried out using a bifunctional thiourea-primary amine catalyst, providing diastereoisomerically and enantiomerically enriched 2-alkyl-2-(arylthio)cyclobutanones having two contiguous stereocenters of which one is a chiral quaternary center. The absolute configuration of these novel adducts was assigned by X-ray diffraction analysis and a transition-state model is proposed to explain the observed stereoselectivities.

Graphical abstract: Deracemizing organocatalyzed Michael addition reactions of 2-(arylthio)cyclobutanones with β-nitrostyrenes

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Supplementary files

Article information


Submitted
19 Jan 2016
Accepted
26 Feb 2016
First published
26 Feb 2016

Org. Biomol. Chem., 2016,14, 3394-3403
Article type
Paper

Deracemizing organocatalyzed Michael addition reactions of 2-(arylthio)cyclobutanones with β-nitrostyrenes

A. Luridiana, A. Frongia, D. J. Aitken, R. Guillot, G. Sarais and F. Secci, Org. Biomol. Chem., 2016, 14, 3394
DOI: 10.1039/C6OB00160B

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