Cobalt-Catalyzed Enantioconvergent Hydrogenation of Minimally Functionalized Isomeric Olefins

被引:29
|
作者
Lu, Peng [1 ]
Wang, Hongliang [1 ,2 ]
Mao, Yihui [1 ]
Hong, Xin [1 ,4 ,5 ,6 ]
Lu, Zhan [1 ,3 ]
机构
[1] Zhejiang Univ, Ctr Chem Frontier Technol, Dept Chem, Hangzhou 310027, Peoples R China
[2] Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Peoples R China
[3] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Peoples R China
[4] Zhejiang Univ, State Key Lab Clean Energy Utilizat, Hangzhou 310027, Peoples R China
[5] Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
[6] Westlake Univ, Sch Sci, Key Lab Precise Synth Funct Mol Zhejiang Prov, Hangzhou 310024, Zhejiang, Peoples R China
基金
国家重点研发计划; 中国国家自然科学基金; 中国博士后科学基金;
关键词
ASYMMETRIC HYDROGENATION; ENANTIOSELECTIVE HYDROGENATION; ALKENES; HYDROFUNCTIONALIZATION; HYDROBORATION;
D O I
10.1021/jacs.2c08525
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Investigation on asymmetric hydrogenation of olefins is of great importance in both pharmaceutical molecule synthesis and chemical industry due to the high demand for enantiopure compounds. The established methods often require geometrically pure olefins. The enantioconvergent reaction provided the possibility to access a single stereoisomer via hydrogenation of E/Z-olefin mixtures; however, a polar functional group next to the carbon-carbon double bond was usually necessary. Here, we reported a cobalt-catalyzed enantioconvergent hydrogenation of readily available minimally functionalized E/Z-olefin mixtures. This strategy shows good functional group tolerance and provides an alternative means to enantioconvergent transformation. The preliminary mechanistic studies indicated that cobalt-catalyzed isomerization was the key to achieve the convergent transformation.
引用
收藏
页码:17359 / 17364
页数:6
相关论文
共 50 条
  • [21] Cobalt-catalyzed hydroazidation of olefins: Convenient access to alkyl azides
    Waser, J
    Nambu, H
    Carreira, EM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (23) : 8294 - 8295
  • [22] Cobalt-catalyzed hydroformylation of olefins in the presence of additional ''inert'' gases
    Piacenti, F
    Calderazzo, F
    Bianchi, M
    Rosi, L
    Frediani, P
    [J]. ORGANOMETALLICS, 1997, 16 (20) : 4235 - 4236
  • [23] COBALT-CATALYZED PHOTOCHEMICAL METHOXYCARBONYLATION OF OLEFINS UNDER AMBIENT CONDITIONS
    TAO, YT
    CHOW, TJ
    LIN, JT
    LIN, CC
    CHIEN, MT
    LIN, CC
    CHOW, YL
    BUONOCORE, GE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (12): : 2509 - 2511
  • [24] Cobalt-catalyzed asymmetric cyclopropanation of electron-deficient olefins
    Chen, Ying
    Ruppel, Joshua V.
    Zhang, X. Peter
    [J]. Journal of the American Chemical Society, 2007, 129 (40): : 12074 - 12075
  • [25] Cobalt-catalyzed biphasic hydroformylation of internal short chain olefins
    Beller, M
    Krauter, JGE
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 143 (1-3) : 31 - 39
  • [26] Cobalt-catalyzed asymmetric cyclopropanation of electron-deficient olefins
    Chen, Ying
    Ruppel, Joshua V.
    Zhang, X. Peter
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (40) : 12074 - +
  • [27] Cobalt-catalyzed dimerization of α-olefins to give linear α-olefin products
    Broene, RD
    Brookhart, M
    Lamanna, WM
    Volpe, AF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) : 17194 - 17195
  • [29] A General Regioselective Synthesis of Alcohols by Cobalt-Catalyzed Hydrogenation of Epoxides
    Liu, Weiping
    Leischner, Thomas
    Li, Wu
    Junge, Kathrin
    Beller, Matthias
    [J]. Advanced Materials, 2020, 132 (28) : 11417 - 11420
  • [30] Cobalt-Catalyzed Asymmetric Sequential Hydroboration/Hydrogenation of Internal Alkynes
    Guo, Jun
    Cheng, Biao
    Shen, Xuzhong
    Lu, Zhan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (43) : 15316 - 15319