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Published on: January 19, 2016
New Strategy To Access Enantioenriched Cyclohexadienones: Kinetic Resolution of para-Quinols by Organocatalytic
Ting Tang1, Nicholas G Moon2, Lydia McKay1
1Department of Chemistry & Biochemistry, Texas Tech University, 1204 Boston Avenue, Lubbock, Texas 79409-1061, United States.
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-of-principle 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.
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