Precise Modulation of BCB Reactive Sites via Lewis/Brønsted Acid Switching for the Synthesis of Spirocycles and Bridged Frameworks.

Org Lett

State Key Laboratory of Natural Product Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P.R. China.

Published: July 2025


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Article Abstract

Bicyclo[1.1.0]butanes (BCBs), which possess multiple switchable reactive sites, serve as the most direct modular scaffolds for constructing benzene ring bioisosteres. Herein, we describe the precise modulation of BCB reactive sites through Lewis/Brønsted acid switching to enable the synthesis of challenging spirocycles and bridged frameworks. The divergent reaction outcomes, arising from the precise control of catalysts over the switchable reactive sites of BCBs, are achieved without any substrate modification.

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http://dx.doi.org/10.1021/acs.orglett.5c02160DOI Listing

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