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One-pot Fluorination and Organocatalytic Robinson Annulation for Asymmetric Synthesis of Mono- and Difluorinated Cyclohexenones.

ABSTRACT: A one-pot fluorination and organocatalytic Robinson annulation sequence has been developed for asymmetric synthesis of 6-fluoroyclohex-2-en-1-ones and 4,6-difluorocyclohex-2-en-1-ones. The reactions promoted by cinchona alkaloid amine afforded products bearing two or three stereocenters in good to excellent yields with up to 99% ee and 20:1 dr.

SUBMITTER: Huang X 

PROVIDER: S-EPMC6225330 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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One-pot Fluorination and Organocatalytic Robinson Annulation for Asymmetric Synthesis of Mono- and Difluorinated Cyclohexenones.

Huang Xin X   Zhao Weizhao W   Zhang Xiaofeng X   Liu Miao M   Vasconcelos Stanley N S SNS   Zhang Wei W  

Molecules (Basel, Switzerland) 20180904 9

A one-pot fluorination and organocatalytic Robinson annulation sequence has been developed for asymmetric synthesis of 6-fluoroyclohex-2-en-1-ones and 4,6-difluorocyclohex-2-en-1-ones. The reactions promoted by cinchona alkaloid amine afforded products bearing two or three stereocenters in good to excellent yields with up to 99% ee and 20:1 dr. ...[more]

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