4.8 Article

A Catalytic Asymmetric Hydrolactonization

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 145, 期 16, 页码 8788-8793

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AMER CHEMICAL SOC
DOI: 10.1021/jacs.3c01404

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In this study, a catalytic asymmetric hydrolactonization using a confined imidodiphosphorimidate (IDPi) Bronsted acid catalyst is reported. The method is simple, scalable, and compatible with a wide variety of substrates. The mechanism and enantioselectivity of this reaction are elucidated through in-depth physicochemical and DFT analyses.
Despite recent advancements in the development of catalytic asymmetric electrophile induced lactonization reactions of olefinic carboxylic acids, the archetypical hydrolactonization has long remained an unsolved and well-recognized challenge. Here, we report the realization of a catalytic asymmetric hydrolactonization using a confined imidodiphosphorimidate (IDPi) Bronsted acid catalyst. The method is operationally simple, scalable, and compatible with a wide variety of substrates. Its potential is showcased with concise syntheses of the sesquiterpenes (-)-boivinianin A and (+)-gossonorol. Through in-depth physicochemical and DFT analyses, we derive a nuanced picture of the mechanism and enantioselectivity of this reaction.

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