Adrien Quintard and Alexandre Alexakis from the University of Geneva report a systematic study on the application and scope of the 1,2-sulfone rearrangement and notably on its asymmetric variant.
A wide variety of nucleophiles can be used to yield highly functionalised substrates, with some demonstrating excellent enantioselectivities of up to 94% ee. This 1,2-sulfone rearrangement constitutes an alternative to the use of expensive 1,1-bis(phenylsulfonyl)ethene and leads to a formal alkylation of the nucleophile.
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1,2-Sulfone rearrangement in organocatalytic reactions
Adrien Quintard and Alexandre Alexakis
Org. Biomol. Chem., 2011, Advance Article