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Enantioselective Synthesis of ?-Functionalized Cyclopentenones and ?-Functionalized Cycloheptenones Utilizing a Redox-Relay Heck Strategy.

ABSTRACT: In this report, the desymmetrization of cyclic enones under relay Heck conditions with an array of aryl boronic acids, alkenyl triflates and indole derivatives is described. This method grants facile access to diverse ?-functionalized cyclopentenones and ?-functionalized cycloheptenones. Using this approach, a formal synthesis of (S)-baclofen was completed in high yield and excellent enantioselectivity.

SUBMITTER: Yuan Q

PROVIDER: S-EPMC7806184 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Enantioselective Synthesis of γ-Functionalized Cyclopentenones and δ-Functionalized Cycloheptenones Utilizing a Redox-Relay Heck Strategy.

Yuan Qianjia Q Prater Matthew B MB Sigman Matthew S MS

Advanced synthesis & catalysis 20191024 2

In this report, the desymmetrization of cyclic enones under relay Heck conditions with an array of aryl boronic acids, alkenyl triflates and indole derivatives is described. This method grants facile access to diverse γ-functionalized cyclopentenones and δ-functionalized cycloheptenones. Using this approach, a formal synthesis of (<i>S</i>)-baclofen was completed in high yield and excellent enantioselectivity. ...[more]

PMID: 33447174

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