Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University, Hangzhou 310024, China.
Institute of Natural Science, Westlake Institute for Advanced Study, Hangzhou 310024, Zhejiang Province, China.
Org Lett. 2023 Apr 7;25(13):2349-2354. doi: 10.1021/acs.orglett.3c00724. Epub 2023 Mar 27.
An organo-photocatalytic sulfonylimination of alkenes was developed by employing readily available -sulfonyl ketimines as bifunctional reagents. This transformation, featuring prominent functional group tolerance, provides a direct and atom-economic approach for the synthesis of valuable β-amino sulfone derivatives as a single regioisomer. In addition to terminal alkenes, internal alkenes participate in this reaction with high diastereoselectivity. -Sulfonyl ketimines with aryl or alkyl substituents were found to be compatible with this reaction condition. This method could be applied in the late-stage modifications of drugs. Additionally, a formal insertion of alkene into cyclic sulfonyl imine was observed, affording a ring expansion product.
一种通过利用易得的 -磺酰基酮亚胺作为双功能试剂的烯烃的有机-光催化磺酰亚胺化反应被开发出来。这种转化具有显著的官能团耐受性，为合成有价值的β-氨基砜衍生物提供了一种直接的、原子经济性的方法，并且产物作为单一区域异构体。除了末端烯烃外，内部烯烃也具有高立体选择性地参与该反应。带有芳基或烷基取代基的 -磺酰基酮亚胺与该反应条件兼容。该方法可应用于药物的后期修饰。此外，还观察到烯烃的环状磺酰亚胺的形式插入，得到环扩张产物。
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