有机催化远程立体控制6-亚甲基-6H-吲哚与异噁唑-5(4H)-酮的氮杂1,8-共轭加成反应  

Organocatalytic Regio-and Enantioselective aza-1,8-Conjugate Additions of Isoxazol-5(4H)-ones to 6-Methide-6H-indoles

作　　者：王兴 宋倩倩 陈续玲 李鹏飞 齐昀坤 李文军[1] Wang Xing;Song Qianqian;Chen Xuling;Li Pengfei;Qi Yunkun;Li Wenjun(School of Pharmacy,Qingdao University,Qingdao,Shandong 266073;Shenzhen Grubbs Institute and Department of Chemistry,Guangdong Provincial Key Laboratory of Catalysis,College of Science,South University of Science and Technology of China,Shenzhen,Guangzhou 518055)

机构地区：[1]青岛大学药学院,山东青岛266073 [2]南方科技大学理学院格拉布斯研究院化学系广东省催化化学重点实验室,广东深圳518055

出　　处：《有机化学》2022年第6期1722-1734,共13页Chinese Journal of Organic Chemistry

基　　金：山东省自然科学基金(No.ZR^(2)021MB026);山东省泰山学者(No.tsqn201812047);深圳市科委创新(No.20200925151614002);广东省催化化学重点实验室(No.2020B121201002)资助项目。

摘　　要：报道了在手性磷酸作用下6-吲哚甲醇原位生成6-亚甲基-6H-吲哚,继而与异噁唑-5(4H)-酮发生不对称1,8-共轭加成反应.该反应实现了异噁唑-5(4H)-酮的对映选择性N-烷基化,以70%~83%的产率和61%~96%的对映选择性得到共轭加成产物.A chiral phosphoric acid catalyzed aza-1,8-conjugate addition of isoxazol-5(4H)-ones to 6-methylene-6H-indoles formed in situ from 6-indolylmethanols has been developed for the first time.Notably,the remote stereocontrolled 1,8-addition of isoxazol-5(4H)-ones was featured by N-selectivity,affording aza-adducts in 70%~83%yields with 61%~96%ee.

关 键 词：不对称有机催化 共轭加成 异噁唑-5(4H)-酮 6-亚甲基-6H-吲哚 

分 类 号：O621.251[理学—有机化学]