Li En, Liao Xiaoyun, Guo Fangfang, Huang Yong, Chen Jiean
Pingshan Translational Medicine Center, Shenzhen Bay Laboratory, Shenzhen 518118, China.
State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
Org Lett. 2024 Sep 13;26(36):7479-7483. doi: 10.1021/acs.orglett.4c02082. Epub 2024 Aug 2.
The field of asymmetric catalysis has been developed by exploring noncovalent interactions, particularly within N-heterocyclic carbene-mediated processes. Despite challenges due to the limited number of compatible electrophiles (predominantly π-acceptors), this study introduces the first asymmetric α-alkylation of 3-aryl oxindoles using C electrophiles. The innovative protocol integrates diverse oxindoles and alkyl, allyl, and propargyl electrophiles, achieving high yields and enantioselectivities. Preliminary mechanistic explorations support a noncovalent catalytic mechanism, enhancing the tool kit for constructing complex chiral molecules with potential applications.
不对称催化领域是通过探索非共价相互作用而发展起来的，尤其是在氮杂环卡宾介导的过程中。尽管由于兼容亲电试剂（主要是π受体）数量有限而面临挑战，但本研究首次报道了使用碳亲电试剂对3-芳基氧化吲哚进行不对称α-烷基化反应。该创新方法整合了多种氧化吲哚以及烷基、烯丙基和炔丙基亲电试剂，实现了高产率和对映选择性。初步的机理探索支持了一种非共价催化机制，为构建具有潜在应用价值的复杂手性分子提供了更多方法。
