SO2-Insertioninducedenantioselectiveoxysulfonylationtoaccessβ-chiralsulfoneswithquaternarycarbonstereocenters<iclass="icon-zqcb"></i>

被引:0
|
作者
Jun Zhang [1 ]
Xuefeng Wang [2 ]
Peiqi Wang [1 ]
Jiayuan Fang [2 ]
Shaoyu Li [1 ]
Jie Wu [1 ,3 ,4 ]
机构
[1] School of Pharmaceutical and Chemical Engineering & Institute for Advanced Studies,Taizhou University
[2] Department of Chemistry,Fudan University
[3] State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences
[4] School of Chemistry and Chemical Engineering,Henan Normal
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O623.83 [亚砜、砜及硫化物];
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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.
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页码:908 / 913
页数:6
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