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SO_(2)-Insertion induced enantioselective oxysulfonylation to access β-chiral sulfones with quaternary carbon stereocenters

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摘要 β-Chiral sulfones are structural motifs widely found in natural products and bioactive molecules, while also serving as important intermediates for the synthesis of valuable chiral scaffolds. In contrast to the rapid growth of sulfur dioxide insertion chemistry over the last decade, enantioselective catalytic variants for accessing β-chiral sulfones, especially those bearing a quaternary carbon stereocenter, remain rare. Herein, we report an enantioselective copper/bisoxazoline catalyzed oxysulfonylation of alkenes to yield isoxazolinyl-containing β-chiral sulfones bearing quaternary carbon stereocenters with moderate to excellent yields and up to 96:4 er. The advantage and irreplaceability of this sulfur dioxide insertion catalytic system have been demonstrated by achieving transformations clearly unavailable with the previously reported sulfonyl chloride system. Additionally,the recoverability of the new-developed bisoxazoline ligand L9 and its reusability without any erosion of the catalytic activity and enantioselectivity further demonstrate the usefulness of the protocol.
出处 《Science China Chemistry》 SCIE EI CAS CSCD 2024年第3期908-913,共6页 中国科学(化学英文版)
基金 supported by the National Natural Science Foundation of China(22171206) the Natural Science Foundation of Zhejiang Province(Z23B020002,LY22B020003,) the Open Foundation of Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers(E22307) the Open Research Fund of School of Chemistry and Chemical Engineering,Henan Normal University(2020ZD04)。
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