N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones

Roxanne L. Atienza, Howard S. Roth, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

65 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1772-1776
Number of pages5
JournalChemical Science
Volume2
Issue number9
DOIs
StatePublished - Sep 2011

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones'. Together they form a unique fingerprint.

Cite this