Catalytic chemo-, regio-, and enantioselective bromochlorination of allylic alcohols

Dennis X Hu; Frederick J Seidl; Cyril Bucher; Noah Z Burns

doi:10.1021/jacs.5b01384

Catalytic chemo-, regio-, and enantioselective bromochlorination of allylic alcohols

J Am Chem Soc. 2015 Mar 25;137(11):3795-8. doi: 10.1021/jacs.5b01384. Epub 2015 Mar 10.

Authors

Dennis X Hu¹, Frederick J Seidl¹, Cyril Bucher¹, Noah Z Burns¹

Affiliation

¹ Department of Chemistry, Stanford University, Stanford, California 94305, United States.

PMID: 25738419
DOI: 10.1021/jacs.5b01384

Abstract

Herein we describe a highly chemo-, regio-, and enantioselective bromochlorination reaction of allylic alcohols, employing readily available halogen sources and a simple Schiff base as the chiral catalyst. The application of this interhalogenation reaction to a variety of substrates, the rapid enantioselective synthesis of a bromochlorinated natural product, and preliminary extension of this chemistry to dibromination and dichlorination are reported.