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1,2-Sulfone rearrangement in organocatalytic reactions
Adrien Quintard1, Alexandre Alexakis
1Department of organic chemistry, University of Geneva Quai Ernest Ansermet 30, 1211 Geneva, Switzerland.
Abstract:
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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