Rhodium-catalyzed asymmetric arylation of allyl sulfones under the conditions of isomerization into alkenyl sulfones

Kelvin Meng-Hui Lim; Tamio Hayashi

doi:10.1021/jacs.5b00216

Rhodium-catalyzed asymmetric arylation of allyl sulfones under the conditions of isomerization into alkenyl sulfones

J Am Chem Soc. 2015 Mar 11;137(9):3201-4. doi: 10.1021/jacs.5b00216. Epub 2015 Feb 25.

Authors

Kelvin Meng-Hui Lim¹, Tamio Hayashi

Affiliation

¹ Department of Chemistry, National University of Singapore , 3 Science Drive 3, Singapore 117543, Singapore.

PMID: 25706689
DOI: 10.1021/jacs.5b00216

Abstract

The reaction of 3-sulfolene with arylboronic acids in the presence of a chiral diene-rhodium catalyst under highly basic conditions (10 equiv of KOH) gave high yields of 3-arylsulfolanes with high enantioselectivity, where 3-sulfolene is in equilibration with 2-sulfolene by base-catalyzed isomerization and the more reactive 2-sulfolene undergoes the rhodium-catalyzed asymmetric arylation.