A facile one-pot sequential conjugate addition/dearomative fluorination transformation of isoxazol-5(4H)-ones with nitroolefins and N-fluorobenzenesulfonimide (NFSI) has been developed. By using a bifunctional chiral tertiary amino-thiourea catalyst, a series of chiral fluorinated isoxazol-5(4H)-ones containing one fluorine-substituted quarternary stereocenter were obtained in high yields with high enantio- and diastereoselectivities. Further transformation of adducts could afford isoxazolidin-5-one derivatives with three contiguous stereocenters.

This one-pot method allows for the synthesis of chiral fluorinated isoxazol-5(4H)-ones with high yields and high enantio- and diastereoselectivities, offering potential for isoxazolidin-5-one derivatives with three con

Paper

Organocatalytic asymmetric one-pot sequential conjugate addition/dearomative fluorination: synthesis of chiral fluorinated isoxazol-5(4H)-ones.

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