Enantioselective Nickel-Catalyzed α‑Spirocyclization of Lactones

Herein we report a strategy for the enantioselective synthesis of spirocycles containing all-carbon quaternary centers via nickel-catalyzed intramolecular addition of lactone enolates to aryl nitriles. The established lactone α-spirocyclization efficiently and enantioselectively forges 5-, 6-, and 7...

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Published inOrganic letters Vol. 26; no. 32; pp. 6793 - 6797
Main Authors Stanko, Allison M., Ramirez, Melissa, de Almenara, Adrian J., Virgil, Scott C., Stoltz, Brian M.
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 16.08.2024
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Letter
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Summary:Herein we report a strategy for the enantioselective synthesis of spirocycles containing all-carbon quaternary centers via nickel-catalyzed intramolecular addition of lactone enolates to aryl nitriles. The established lactone α-spirocyclization efficiently and enantioselectively forges 5-, 6-, and 7-membered rings, performing best in the synthesis of 7-membered rings (up to 90% ee). This discovery represents an expansion of the synthetic toolkit for enantioselective spirocyclization, providing access to chiral, pharmaceutically relevant spirocyclic products.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c01661