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Royal Society of Chemistry, Organic and Biomolecular Chemistry, 13(14), p. 3394-3403, 2016

DOI: 10.1039/c6ob00160b

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

Journal article published in 2016 by Alberto Luridiana ORCID, Angelo Frongia ORCID, David-J. Aitken, Regis Guillot, Giorgia Sarais, Francesco Secci
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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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.