N-heterocyclic carbenes (NHCs) are Lewis basic small molecules that can be used as alternatives to metal catalysts to facilitate organic transformations.  In contrast to established methods (1,2 or 1,4 addition of the NHC to an aldehyde or a,�-unsaturated carbonyl compound, respectively), a new reactivity mode has been discovered, proceeding through the carbene addition to a vinyl sulfone. The new NHC process utilizes 1,1-bis(phenylsulfonyl)ethylene as a substrate to access the isoxazolidine motif through a carbene-catalyzed rearrangement.

<i>N</i>-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones facilitating an efficient [3+2] dipolar cycloaddition

239th National Meeting (2010)

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N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones facilitating an efficient [3+2] dipolar cycloaddition