Ni-Catalyzed enantioselective reductive aryl-alkenylation of alkenes: application to the synthesis of (+)-physovenine and (+)-physostigmine

被引:63
|
作者
Li, Yuxiu [1 ]
Ding, Zhengtian [1 ]
Lei, Aiwen [1 ]
Kong, Wangqing [1 ]
机构
[1] Wuhan Univ, Coll Chem & Mol Sci, IAS, Wuhan 430072, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
CROSS-COUPLING REACTIONS; ANION CAPTURE PROCESSES; FORMAL TOTAL SYNTHESIS; ASYMMETRIC-SYNTHESIS; CALABAR ALKALOIDS; CYCLIZATION; OXINDOLES; HALIDES; ROUTE; DICARBOFUNCTIONALIZATION;
D O I
10.1039/c9qo00744j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Ni-catalyzed enantioselective reductive aryl-alkenylation of alkenes by cyclizative coupling of an aryl bromide and a vinyl bromide is developed, providing efficient access to functionalized 3,3-disubstituted oxindoles under mild conditions, without requiring the use of preformed vinylmetallic reagents. With this method, a concise formal synthesis of (+)-physovenine and (+)-physostigmine has been completed.
引用
收藏
页码:3305 / 3309
页数:5
相关论文
共 50 条
  • [31] Reaction Mechanism for the Ni-Catalyzed Reductive Cross-Coupling of Aryl Halides
    Jiang Feng
    Ren Qing-Hua
    ACTA PHYSICO-CHIMICA SINICA, 2014, 30 (05) : 821 - +
  • [32] Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction
    Isshiki, Ryota
    Kurosawa, Miki B.
    Muto, Kei
    Yamaguchi, Junichiro
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (27) : 10333 - 10340
  • [33] Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation
    Mills, L. Reginald
    Graham, Joshua M.
    Patel, Purvish
    Rousseaux, Sophie A. L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (49) : 19257 - 19262
  • [34] Ni-catalyzed reductive alkylgermylation of activated alkenes: Modular access to polyfunctionalized alkyl germanes
    Qiao, Yi-Wei
    Zhou, Bing-Qi
    Huang, Yuan
    CHEM CATALYSIS, 2023, 3 (12):
  • [35] Sn-Free Ni-Catalyzed Reductive Coupling of Glycosyl Bromides with Activated Alkenes
    Gong, Hegui
    Andrews, R. Stephen
    Zuccarello, Joseph L.
    Lee, Stephen J.
    Gagne, Michel R.
    ORGANIC LETTERS, 2009, 11 (04) : 879 - 882
  • [36] Palladium-Catalyzed Enantioselective Heck Carbonylation with a Monodentate Phosphoramidite Ligand: Asymmetric Synthesis of (+)-Physostigmine, (+)-Physovenine, and (+)-Folicanthine
    Chen, Ming
    Wang, Xucai
    Yang, Pengfei
    Kou, Xun
    Ren, Zhi-Hui
    Guan, Zheng-Hui
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (29) : 12199 - 12205
  • [37] Ni-catalyzed two-component reductive dicarbofunctionalization of alkenes via radical cyclization
    Kuang, Yulong
    Wang, Xuefeng
    Anthony, David
    Diao, Tianning
    CHEMICAL COMMUNICATIONS, 2018, 54 (20) : 2558 - 2561
  • [38] Palladium-Catalyzed Enantioselective Heck Carbonylation with a Monodentate Phosphoramidite Ligand: Asymmetric Synthesis of (+)-Physostigmine, (+)-Physovenine, and (+)-Folicanthine
    Chen, Ming
    Wang, Xucai
    Yang, Pengfei
    Kou, Xun
    Ren, Zhi-Hui
    Guan, Zheng-Hui
    Advanced Materials, 2020, 132 (29) : 12297 - 12303
  • [39] Ni-Catalyzed Alkenylation of Triazolopyridines: Synthesis of 2,6-Disubstituted Pyridines
    Liu, Sheng
    Sawicki, James
    Driver, Tom G.
    ORGANIC LETTERS, 2012, 14 (14) : 3744 - 3747
  • [40] Exploration of Quinim Ligand in Ni-Catalyzed Enantioselective Reductive Carbamoyl-Alkylation of Alkene
    Wu Licheng
    Wu Xianqing
    Qu Jingping
    Chen Yifeng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (12) : 4239 - 4250