Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (6): 1722-1734.DOI: 10.6023/cjoc202112023 Previous Articles     Next Articles

ARTICLES

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

王兴a, 宋倩倩a, 陈续玲b, 李鹏飞b,*(), 齐昀坤a,*(), 李文军a,*()   

  1. a 青岛大学药学院 山东青岛 266073
    b 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
  • 收稿日期:2021-12-18 修回日期:2022-02-28 发布日期:2022-03-08
  • 通讯作者: 李鹏飞, 齐昀坤, 李文军
  • 作者简介:
    † 共同第一作者
  • 基金资助:
    山东省自然科学基金(ZR2021MB026); 山东省泰山学者(tsqn201812047); 深圳市科委创新(20200925151614002); 广东省催化化学重点实验室(2020B121201002)

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

Xing Wanga, Qianqian Songa, Xuling Chenb, Pengfei Lib(), Yunkun Qia(), Wenjun Lia()   

  1. a School of Pharmacy, Qingdao University, Qingdao, Shandong 266073
    b 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
  • Received:2021-12-18 Revised:2022-02-28 Published:2022-03-08
  • Contact: Pengfei Li, Yunkun Qi, Wenjun Li
  • About author:
    † These authors contributed equally to this work
  • Supported by:
    Natural Science Foundation of Shandong Province(ZR2021MB026); Special Funds of the Taishan Scholar Program of Shandong Province(tsqn201812047); Shenzhen Innovation of Science and Technology Commission(20200925151614002); Guangdong Provincial Key Laboratory of Catalysis(2020B121201002)

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.

Key words: asymmetric organocatalysis, conjugate addition, isoxazol-5(4H)-ones, 6-methylene-6H-indole