HOT: Studying the scope of the 1,2-sulfone rearrangement

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.

Both reviewers thought this HOT article would be of very wide interest in the organic community and it is now free to access until 8th February.

1,2-Sulfone rearrangement in organocatalytic reactions
Adrien Quintard and Alexandre Alexakis
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00818D

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One Response to “HOT: Studying the scope of the 1,2-sulfone rearrangement”

  1. Alexandre Alexakis says:

    Indeed, the described 1,2-sulfone rearrangement displays several interesting aspects for organocatalysis. The described reactivity can have implications for the development of new 1,2-Michael acceptors, new rearrangement, and toward a better understanding of aminocatalysis.

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