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New Strategy To Access Enantioenriched Cyclohexadienones: Kinetic Resolution of para-Quinols by Organocatalytic Thiol-Michael Addition Reactions.

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.

SUBMITTER: Tang T

PROVIDER: S-EPMC6643461 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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New Strategy To Access Enantioenriched Cyclohexadienones: Kinetic Resolution of <i>para</i>-Quinols by Organocatalytic Thiol-Michael Addition Reactions.

Tang Ting T Moon Nicholas G NG McKay Lydia L Harned Andrew M AM

ACS omega 20181114 11

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 <i>para</i>-quinol ...[more]

PMID: 31458205

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