Radical cascade cyclization reaction is one of the most attractive synthetic strategies for the construction of polycyclic molecules. While diastereoselective synthesis of natural products and complex molecules has been well established, the enantioselective radical cascade cyclization is a long-standing challenge and need to be solved. Herein, We disclosed the asymmetric radical bicylization of 1,6-enynes with diazo compounds via Co(II)-based metalloradical catalyst with well controlling of both enantioselectivity and diastereoselectivity. The key to the success is the judicious selection of <i>D<sub>2</sub></i>-symmetric chiral amidoporphyrins as the supporting ligands. Systematic experimental and computational studies shed light on the underlying stepwise radical mechanism. The obtained enantioenriched cyclopropane-fused tetrahydrofurans may serve as useful intermediates for stereoselective organic synthesis which was showcased by several stereospecific transformations.

Radical cascade cyclization for construction of chiral bicyclic structures via Co(II)-based metalloradical catalysis

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