Copper-Catalyzed Remote Enantioselective Sulfonylation of Yne-Allylic Esters with Sodium Sulfinates

被引:21
|
作者
Li, Meng-Die [1 ]
Wang, Zi-Han [1 ]
Zhu, Hui [1 ]
Wang, Xin-Ru [1 ]
Wang, Jia-Run [1 ]
Lin, Tao-Yan [1 ]
机构
[1] Huaibei Normal Univ, Sch Chem & Mat Sci, Key Lab Green & Precise Synthet Chem & Applicat, Minist Educ, Huaibei 235000, Anhui, Peoples R China
关键词
Asymmetric Catalysis; Copper; Remote Substitution; Sulfur; ASYMMETRIC PROPARGYLIC SUBSTITUTION; FORMAL 3+2 CYCLOADDITION; BETA-KETOESTERS; AMINES; QUATERNARY; ALCOHOLS; ETHERIFICATION; CONSTRUCTION; AMINATION; ACETATES;
D O I
10.1002/anie.202313911
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Impressive progress has been made in the copper-catalyzed asymmetric propargylic substitution (APS) reaction, but its use in remote asymmetric yne-allylic substitution remains a challenging topic. Herein, we report the first remote enantioselective copper-catalyzed sulfonylation of yne-allylic esters with sodium sulfinates. The reaction is assumed to occur via a copper-vinylvinylidene species as the key reactive intermediate. The use of readily available starting materials, the mild reaction conditions, and the excellent regio-, enantio- and stereoselectivity, as well as broad substrate scope (>70 examples), show the practicality and attractiveness of this method.
引用
收藏
页数:6
相关论文
共 50 条
  • [21] Copper-catalyzed Enantioselective Intramolecular Alkylboron Allylic Alkylation
    Hojoh, Kentaro
    Shido, Yoshinori
    Ohmiya, Hirohisa
    Sawamura, Masaya
    CHEMISTRY LETTERS, 2018, 47 (05) : 632 - 635
  • [22] Copper-catalyzed enantioselective allylic oxidation of acyclic olefins
    Zhang, Bo
    Zhu, Shou-Fei
    Zhou, Qi-Lin
    TETRAHEDRON LETTERS, 2013, 54 (21) : 2665 - 2668
  • [23] Copper-Catalyzed Remote para-C-H Functionalization of Anilines with Sodium and Lithium Sulfinates
    Liang, Shuai
    Bolte, Michael
    Manolikakes, Georg
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (01) : 96 - 100
  • [24] Copper-catalyzed stereoselective sulfonylations of alkynes using sodium sulfinates
    Taniguchi, Nobukazu
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [25] Copper-catalyzed electrophilic amination of sodium sulfinates at room temperature
    Zhu, Haibo
    Shen, Yajing
    Deng, Qinyue
    Tu, Tao
    CHEMICAL COMMUNICATIONS, 2015, 51 (92) : 16573 - 16576
  • [26] Copper-catalysed asymmetric annulation of yne-allylic esters with amines to access axially chiral arylpyrroles
    Yao, Chaochao
    Li, Dan-Ran
    Xiang, Hua-Ming
    Li, Si-Jia
    Lu, Yuepeng
    Wang, Zihao
    Yin, Tingrui
    Wang, Jiaqiang
    Feng, Kongling
    Zhu, Cuiju
    Xu, Hao
    NATURE COMMUNICATIONS, 2024, 15 (01)
  • [27] Copper-catalyzed sulfonamides formation from sodium sulfinates and amines
    Tang, Xiaodong
    Huang, Liangbin
    Qi, Chaorong
    Wu, Xia
    Wu, Wanqing
    Jiang, Huanfeng
    CHEMICAL COMMUNICATIONS, 2013, 49 (54) : 6102 - 6104
  • [28] Copper-Catalyzed Asymmetric Allylic Alkylation of -Keto Esters with Allylic Alcohols
    Trillo, Paz
    Baeza, Alejandro
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (10) : 1735 - 1741
  • [29] Highly enantioselective copper-catalyzed allylic alkylation with phosphoramidite ligands
    van Zijl, AW
    Arnold, LA
    Minnaard, AJ
    Feringa, BL
    ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (04) : 413 - 420
  • [30] Copper-catalyzed enantioselective allylic cross-coupling with alkylboranes
    Hojoh, Kentaro
    Shido, Yoshinori
    Nagao, Kazunori
    Mori, Seiji
    Ohmiya, Hirohisa
    Sawamura, Masaya
    TETRAHEDRON, 2015, 71 (37) : 6519 - 6533