Design, preparation, and implementation of an imidazole-based chiral biaryl P,N-ligand for asymmetric catalysis

Flavio S P Cardoso; Khalil A Abboud; Aaron Aponick

doi:10.1021/ja407689a

Design, preparation, and implementation of an imidazole-based chiral biaryl P,N-ligand for asymmetric catalysis

J Am Chem Soc. 2013 Oct 2;135(39):14548-51. doi: 10.1021/ja407689a. Epub 2013 Sep 17.

Authors

Flavio S P Cardoso¹, Khalil A Abboud, Aaron Aponick

Affiliation

¹ Department of Chemistry, University of Florida , P.O. Box 117200, Gainesville, Florida 32611, United States.

PMID: 24044433
DOI: 10.1021/ja407689a

Abstract

A new strategy for increasing the barrier to rotation in biaryls has been developed that allows for the incorporation of 5-membered aromatic heterocycles into chiral atropisomers. Using this concept, an imidazole-based biaryl P,N-ligand has been designed and prepared as a single enantiomer. This ligand performs exceptionally well in the enantioselective A(3)-coupling, demonstrating the potential of this new design element.