ChemInform Abstract: N‐Heterocyclic Carbene‐Catalyzed Rearrangements of Vinyl Sulfones.

Abstract

N-Heterocyclic Carbene-Catalyzed Rearrangements of Vinyl Sulfones. -The carbene generated from a triazolium salt and NaOtBu catalyzes the rearrangement of 1,1-bis(arylsulfonyl)ethenes to the corresponding (E)-1,2-bis(arylsulfonyl)ethenes. The combination of this rearrangement with a subsequent [3 + 2] cycloaddition reaction to a nitrone in a single flask provides highly substituted isoxazolines as single diastereomers. The method can be also applied to the [3 + 2] cycloaddition reaction of azomethine imine (X). -(ATIENZA, R. L.; ROTH, H. S.; SCHEIDT*, K. A.; Chem. Sci. 2 (2011) 9, 1772-1776, http://dx.doi.org/10.1039/c1sc00194a ; Dep. Chem., Northwest. Univ., Evanston, IL 60208, USA; Eng.) -Klein 52-125