Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
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N-Heterocyclic Carbene-Promoted Rauhut–Currier Reactions between Vinyl Sulfones and α,β-Unsaturated Aldehydes

Roxanne L. Atienza A and Karl A. Scheidt A B

A Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Silverman Hall, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA.

B Corresponding author. Email: scheidt@northwestern.edu

Australian Journal of Chemistry 64(8) 1158-1164 http://dx.doi.org/10.1071/CH11264
Submitted: 8 July 2011  Accepted: 19 July 2011   Published: 19 August 2011

Abstract

N-heterocyclic carbenes (NHCs) promote the addition of 1,1-bis(phenylsulfonyl)ethylene to the α-position of α,β-unsaturated aldehydes. The proposed reaction pathway for this Rauhut–Currier-type reaction includes an unusual conjugate addition of an NHC to a bis-vinyl sulfone.

Graphical Abstract Image


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