New Strategy To Access Enantioenriched Cyclohexadienones: Kinetic Resolution of para-Quinols by Organocatalytic Thiol-Michael Addition Reactions
Date
2018-11-14
Journal Title
Journal ISSN
Volume Title
Publisher
American Chemical Society
Abstract
Existing stereoselective routes to 2,5-cyclohexadienones involve either desymmetrization of an achiral substrate or have attempted to perform an asymmetric dearomatization of a phenol. Herein, we report proof-ofprinciple experiments aimed at developing a kinetic resolution as an alternative method for accessing enantioenriched 2,5-cyclohexadienones. More specifically, chiral bifunctional thiourea catalysts were used to promote the addition of 2-thionapthalene into unsymmetric para-quinols. The selectivity of the kinetic resolution was found to be quite sensitive to substitution around the substrate.
Description
Keywords
Natural Sciences, Organic Chemistry, Asymmetric Catalysis, Kinetic Resolution
Citation
ACS Omega, 2018, 3, 15492-15500