title: N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones.
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.
authors.affiliation: Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, 2145 Sheridan Road, Evanston, IL, 60208, USA;
authors.forename: Roxanne L
authors.initials: RL
authors.lastname: Atienza
authors.forename: Howard S
authors.initials: HS
authors.lastname: Roth
authors.forename: Karl A
authors.initials: KA
authors.lastname: Scheidt