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.
Titolo: | Deracemizing organocatalyzed Michael addition reactions of 2-(arylthio)cyclobutanones with β-nitrostyrenes |
Autori: | |
Data di pubblicazione: | 2016 |
Rivista: | |
Handle: | http://hdl.handle.net/11584/182518 |
Tipologia: | 1.1 Articolo in rivista |
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