N-heterocyclic Carbene-catalyzed Rearrangements of Vinyl Sulfones

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2012 Mar 27

PMID 22448316

Citations 6

Authors

Roxanne L Atienza

Howard S Roth

Karl A Scheidt

Affiliations

Soon will be listed here.

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.

Citing Articles

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NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy-Breslow Intermediates.

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Dipolar addition to cyclic vinyl sulfones leading to dual conformation tricycles.

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