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Divergent Synthesis of Bicyclo[3.2.1]octenes and Cyclohexenes via Catalytic Annulations of Nazarov Reagent and Vinyl 1,2-Diketones.

Bicyclo[3.2.1]octanes and related structures are unique units that widely exist in natural products, but the rapid and stereoselective construction of this skeleton is a challenging issue. We report the stereodivergent synthesis of bicyclo[3.2.1]octenes using Nazarov reagents and alkenyl 1,2-diketones with Brønsted base catalysis under mild conditions. Both stereoisomers of the bridged products can be obtained by tuning the reaction conditions, and cyclohexene product can also be selectively formed.