Issue 5, 2011

1,2-Sulfone rearrangement in organocatalytic reactions

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.

Graphical abstract: 1,2-Sulfone rearrangement in organocatalytic reactions

Supplementary files

Article information

Article type
Paper
Submitted
03 Oct 2010
Accepted
10 Nov 2010
First published
07 Jan 2011

Org. Biomol. Chem., 2011,9, 1407-1418

1,2-Sulfone rearrangement in organocatalytic reactions

A. Quintard and A. Alexakis, Org. Biomol. Chem., 2011, 9, 1407 DOI: 10.1039/C0OB00818D

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