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1,2-Sulfone rearrangement in organocatalytic reactions. | LitMetric

1,2-Sulfone rearrangement in organocatalytic reactions.

Org Biomol Chem

Department of organic chemistry, University of Geneva Quai Ernest Ansermet 30, 1211 Geneva, Switzerland.

Published: March 2011

The 1,2-sulfone rearrangement resulting from nucleophilic addition to bis activated vinyl-sulfones has been studied in more detail. Various nucleophiles activated by different types of catalysts (enamine, Brönsted base, thiourea) are able to promote such rearrangement in excellent yields and moderate to excellent enantioselectivities (up to 94% ee). Mechanistic studies have led to a better understanding of the mechanism and allowed its application to other electrophiles such as vinyl-sulfone acrylates.

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Source
http://dx.doi.org/10.1039/c0ob00818dDOI Listing

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