Highly enantioselective benzoin condensation reactions involving a bifunctional protic pentafluorophenyl-substituted triazolium precatalyst

Louise Baragwanath; Christopher A Rose; Kirsten Zeitler; Stephen J Connon

doi:10.1021/jo902018j

Highly enantioselective benzoin condensation reactions involving a bifunctional protic pentafluorophenyl-substituted triazolium precatalyst

J Org Chem. 2009 Dec 4;74(23):9214-7. doi: 10.1021/jo902018j.

Authors

Louise Baragwanath¹, Christopher A Rose, Kirsten Zeitler, Stephen J Connon

Affiliation

¹ Centre for Synthesis and Chemical Biology, School of Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland.

PMID: 19950884
DOI: 10.1021/jo902018j

Abstract

Improved catalyst design by incorporating 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 archetypal benzoin condensation with excellent efficiency and unprecedented enantioselectivity.