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A Catalytic Asymmetric Hydrolactonization.

ABSTRACT: 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) Brønsted 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.

SUBMITTER: Maji R

PROVIDER: S-EPMC10141295 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature

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A Catalytic Asymmetric Hydrolactonization.

Maji Rajat R Ghosh Santanu S Grossmann Oleg O Zhang Pinglu P Leutzsch Markus M Tsuji Nobuya N List Benjamin B

Journal of the American Chemical Society 20230412 16

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) Brønsted acid catalyst. The method is operationally simple, scalable, and compatible with a wide variety of substrates. Its potential ...[more]

PMID: 37043821

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