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Chemistry Weekly Seminar - Dr. Michel Gravel

Posted on 2017-09-01 in Events
Sep 8, 2017

Title: Organocatalysis Using N-Heterocyclic Carbenes

N-Heterocyclic carbenes (NHCs) are well known for their ability to catalytically generate nucleophilic acyl anion equivalents from aldehydes. This catalytic manifold is best exemplified by the benzoin and Stetter reactions generating a-hydroxyketones and 1,4-dicarbonyl products, respectively. However, some of the most synthetically useful substrate combinations are not currently amenable to reactions in high chemo- or enantioselectivity. For instance, the use of two distinct aldehydes in the cross-benzoin reaction or of simple unsaturated ketones in the intermolecular Stetter reaction do not generally provide products in high yield and/or enantiomeric ratio. We have recently made some headway in addressing both of these challenges through the use of triazolium, oxazolium, and bis(dialkylamino)cyclopropenium salts. Our progress in improving the scope as well as the chemo- and stereoselectivity of these classical reactions will be presented.

Date: Friday, September 8, 2017
Time: 4:00 p.m.
Location: Thorvaldson 105

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