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Desymmetrization of Cyclohexadienones via [3+2]/[2+1] Domino Annulation: Access to Cyclopropane Fused Tricyclic Enones

Yannan Zhu, Sen Wang, Bo Fang, Qiuyun Li, Gang Qi, Zhongfei Han

2024Advanced Synthesis & Catalysis15 citationsDOI

Abstract

Abstract A [3+2]/[2+1] domino annulation reaction of cyclohexadienones and α‐aryl vinylsulfonium salts has been reported. A range of cyclopropane fused tricyclic enones bearing four contiguous stereocenters were obtained as a single diastereomer in 44–93% yields. The synthetic utility was demonstrated with the gram‐scale reactions and further transformations of the products.

Topics & Concepts

ChemistryAnnulationDominoDesymmetrizationTricyclicCyclopropaneStereochemistryRing (chemistry)Organic chemistryCatalysisEnantioselective synthesisCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsAsymmetric Synthesis and Catalysis