Precise Modulation of BCB Reactive Sites via Lewis/Brønsted Acid Switching for the Synthesis of Spirocycles and Bridged Frameworks
Ming‐Ming Li, Tengfei Xiao, Yi-Xiang Geng, Guo‐Qiang Xu, Peng‐Fei Xu
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.
Topics & Concepts
ChemistryBrønsted–Lowry acid–base theoryLewis acids and basesModulation (music)Combinatorial chemistryCatalysisOrganic chemistryAestheticsPhilosophyAsymmetric Synthesis and CatalysisChemical synthesis and alkaloidsChemical Synthesis and Analysis