Tunable Diastereoselective Desymmetrization of Cyclohexadienones Triggered by Copper-Catalyzed Three-Component Coupling Reaction

• DOI: 10.1021/acs.joc.7b00936
• Publication Date: 2017-06-11T13:48:42Z
• Authors: Raghunath Reddy A...; Rambabu Chegondi
• Keywords: 01 natural sciences; 0104 chemical sciences

Catalytic tandem diastereoselective desymmetrization of cyclohexadienone-containing 1,6-enynes has been achieved through copper-catalyzed [3 + 2]-cycloaddition followed by ketenimine formation and subsequent intramolecular conjugate addition. The cascade reaction provides cis-hydrobenzofurans in good yields with excellent diastereoselectivity. The exo- or endo-selectivity of bicyclic scaffolds depends on the selection of the base in the reaction. In addition, N-tethered bicyclic products further transformed into tricyclic compounds via intramolecular Michael addition.