Access to Quaternary‐Substituted Cyclobutylsilanes by Ring Opening of Arylbicyclobutanes with Silyllithium Reagents

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Abstract: Disclosed herein is the reaction of silyllithium reagents with quaternary‐substituted arylbicyclobutanes to diastereoselectively form polysubstituted cyclobutylsilanes by C−C bond cleavage. The bicyclobutanes are generated in situ, by lithium‐halogen exchange, from readily accessible (bromomethyl) iodocyclopropane precursors, rendering this a one‐pot transformation. The trapping of a generated cyclobutyllithium intermediate with an electrophile was also demonstrated, providing a cyclobutane product with vicinal quaternary stereocenters. The utility of the cyclobutylsilane products was showcased by Tamao−Fleming oxidation to prepare a quaternary‐substituted cyclobutanol.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Access to Quaternary‐Substituted Cyclobutylsilanes by Ring Opening of Arylbicyclobutanes with Silyllithium Reagents ; day:10 ; month:02 ; year:2025 ; extent:6
Angewandte Chemie / International edition. International edition ; (10.02.2025) (gesamt 6)

Creator: Sercel, Zachary P.
Marek, Ilan

DOI: 10.1002/anie.202421235

URN: urn:nbn:de:101:1-2502111329015.740732392045

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:29 AM CEST

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Associated

Sercel, Zachary P.
Marek, Ilan

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