Highly Enantioselective Benzoin Condensation Reactions Involving a Bifunctional Protic Pentafluorophenyl-Substituted Triazolium Precatalyst
Louise Baragwanath, Christopher A. Rose, Kirsten Zeitler and Stephen J. Connon*
*Centre for Synthesis and Chemical Biology, School of
Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland, Email:
connons
tcd.ie
L. Baragwanath, C. A. Rose, K. Zeitler, S. J. Connon, J. Org. Chem., 2009, 74, 9214-9217.
DOI: 10.1021/jo902018j
Abstract
A hydrogen bond donating substituent to improve enantiocontrol together with an acidifying pentafluorophenyl substituent to enhance catalyst efficiency results in a triazolium ion precatalyst that promotes the asymmetric benzoin condensation with excellent efficiency and unprecedented enantioselectivity.
see article for more examples
Key Words
acyloins, asymmetric catalysis, benzoin condensation, carbenes, triazolium salts, organocatalysis
ID: J42-Y2009-3520
