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Issue 9, 2011
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N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones

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Abstract

N-heterocyclic carbenes catalyze the rearrangement of 1,1-bis(arylsulfonyl)ethylene to the corresponding trans-1,2-bis(phenylsulfonyl) under mild conditions. Tandem rearrangement/cycloadditions have been developed to capitalize on this new process and generate highly substituted isoxazolines and additional heterocyclic compounds. Preliminary mechanistic studies support a new conjugate addition/Umpolung process involving the ejection and subsequent unusual re-addition of a sulfinate ion.

Graphical abstract: N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones

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Publication details

The article was received on 28 Mar 2011, accepted on 19 May 2011 and first published on 10 Jun 2011


Article type: Edge Article
DOI: 10.1039/C1SC00194A
Chem. Sci., 2011,2, 1772-1776

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    N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones

    R. L. Atienza, H. S. Roth and K. A. Scheidt, Chem. Sci., 2011, 2, 1772
    DOI: 10.1039/C1SC00194A

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