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Journal Article

A Catalytic Asymmetric Hydrolactonization

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Maji,  Rajat
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Ghosh,  Santanu
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Grossmann,  Oleg
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Zhang,  Pinglu
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Leutzsch,  Markus
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo 001-0021, Japan;

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Citation

Maji, R., Ghosh, S., Grossmann, O., Zhang, P., Leutzsch, M., Tsuji, N., et al. (2023). A Catalytic Asymmetric Hydrolactonization. Journal of the American Chemical Society, 145(16), 8788-8793. doi:10.1021/jacs.3c01404.


Cite as: https://hdl.handle.net/21.11116/0000-000D-0691-8
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.