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Gold-Catalyzed Synthesis of Chiral Cyclopentadienyl Esters via Chirality Transfer.

ABSTRACT: Efficient access to chiral cyclopentadienyl esters from readily accessible chiral enynyl ester substrates is developed. Typically high levels of chirality transfer realized in this homogeneous gold catalysis are attributed to the intermediacy of a chiral bent allene gold complex. Cyclopentadienyl esters can be prepared in good yields and with excellent enantiomeric excesses. The synthetic utilities of the chiral cyclopentadienyl esters are demonstrated by the Diels-Alder reactions, fluorination, alkylation, and epoxidation without any notable erosion of enantiopurity.

SUBMITTER: Zhao K

PROVIDER: S-EPMC8623356 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Gold-Catalyzed Synthesis of Chiral Cyclopentadienyl Esters via Chirality Transfer.

Zhao Ke K Hsu Yu-Chen YC Yang Ziguang Z Liu Rai-Shung RS Zhang Liming L

Organic letters 20200810 16

Efficient access to chiral cyclopentadienyl esters from readily accessible chiral enynyl ester substrates is developed. Typically high levels of chirality transfer realized in this homogeneous gold catalysis are attributed to the intermediacy of a chiral bent allene gold complex. Cyclopentadienyl esters can be prepared in good yields and with excellent enantiomeric excesses. The synthetic utilities of the chiral cyclopentadienyl esters are demonstrated by the Diels-Alder reactions, fluorination, ...[more]

PMID: 32806155

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