Regiodivergent Lewis acid catalysis of bicyclo[1.1.0]butanes with 2-naphthols.

ABSTRACT: Enhancing drug efficacy often involves increasing the proportion of sp³-hybridized carbons. Three-dimensional polycyclic frameworks, such as bicyclo[1.1.1]pentanes (BCPs) and bicyclo[2.1.1]hexanes (BCHs), serve as excellent benzene bioisosteres, improving bioavailability and reducing toxicity while retaining biological activity. However, synthetic routes to 2D/3D-ring-fused BCHs via dearomatization are scarce, previously limited to cycloadditions of bicyclobutanes (BCBs) with indoles, bicyclic aza-arenes, or naphthalenes. Herein, we achieve Lewis acid-catalyzed dearomatization of BCBs with 2-naphthol. Eu(OTf)₃ catalysis provides dearomatized tertiary alcohols, while AgBF₄ promotes dearomatization/aromatization to directly access naphthalene-fused BCH

SUBMITTER: Fan L 

PROVIDER: S-EPMC12418247 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature