Rhodium-catalyzed enantioselective annulation of N-phenoxyacetamides with 1,3-dienes

被引:6
|
作者
Yang, Hui [1 ]
Yang, Zi-Qi [1 ]
Zhang, Su-Zhen [1 ]
Zhang, Wen-Wen [1 ]
Gu, Qing [1 ]
You, Shu-Li [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
asymmetric catalysis; C-H functionalization; rhodium catalysis; chiral dihydrobenzofuran; C-H FUNCTIONALIZATION; ASYMMETRIC HYDROGENATION; BOND FUNCTIONALIZATION; ACTIVATION; RH; DERIVATIVES; BENZOFURAN; ALKYLATION; AMIDATION; COMPLEXES;
D O I
10.1007/s11426-023-1637-8
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chiral dihydrobenzofuran is a valuable synthetic fragment in both medicinal and organic chemistry. Efficient rhodium(III)-catalyzed chemoselective and enantioselective C-H functionalization/[3+2] annulation of N-phenoxyacetamides with 1,3-dienes is reported. In the presence of 5 mol% CpRh complex, various chiral dihydrobenzofurans were synthesized in up to 79% yield and 98% ee. This reaction proceeds under mild conditions with excellent functional group compatibility.
引用
收藏
页码:2842 / 2846
页数:5
相关论文
共 50 条
  • [1] Rhodium-catalyzed enantioselective annulation of N-phenoxyacetamides with 1,3-dienes
    Hui Yang
    Zi-Qi Yang
    Su-Zhen Zhang
    Wen-Wen Zhang
    Qing Gu
    Shu-Li You
    Science China(Chemistry), 2023, 66 (10) : 2842 - 2846
  • [2] Rhodium-catalyzed enantioselective annulation of N-phenoxyacetamides with 1,3-dienes
    Hui Yang
    Zi-Qi Yang
    Su-Zhen Zhang
    Wen-Wen Zhang
    Qing Gu
    Shu-Li You
    Science China(Chemistry), 2023, (10) : 2842 - 2846
  • [3] Rhodium-catalyzed enantioselective annulation of N-phenoxyacetamides with 1,3-dienes
    Hui Yang
    Zi-Qi Yang
    Su-Zhen Zhang
    Wen-Wen Zhang
    Qing Gu
    Shu-Li You
    Science China Chemistry, 2023, 66 : 2842 - 2846
  • [4] Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes
    Yang, Xiao-Hui
    Dong, Vy M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (05) : 1774 - 1777
  • [5] Rhodium-catalyzed hydrofunctionalization: Enantioselective coupling of indolines and 1,3-dienes
    Dong, Vy M. (dongv@uci.edu), 1774, American Chemical Society (139):
  • [6] Rh(III)-Catalyzed C-H Activation/[3+2] Annulation of N-Phenoxyacetamides via Carbooxygenation of 1,3-Dienes
    Wu, Liexin
    Li, Liping
    Zhang, Haiman
    Gao, Hui
    Zhou, Zhi
    Yi, Wei
    ORGANIC LETTERS, 2021, 23 (10) : 3844 - 3849
  • [7] Rhodium-catalyzed isomerization of unactivated alkynes to 1,3-dienes
    Shintani, Ryo
    Duan, Wei-Liang
    Park, Soyoung
    Hayashi, Tamio
    CHEMICAL COMMUNICATIONS, 2006, (34) : 3646 - 3647
  • [8] (CDC)-Rhodium-Catalyzed Hydroallylation of Vinylarenes and 1,3-Dienes with AllylTrifluoroborates
    Marcum, Justin S.
    Cervarich, Tia N.
    Manan, Rajith S.
    Roberts, Courtney C.
    Meek, Simon J.
    ACS CATALYSIS, 2019, 9 (07) : 5881 - 5889
  • [9] Mechanism of regioselectivity of rhodium-catalyzed hydrothiolation of 1,3-dienes: A computational study
    Yu, Xianjie
    Shen, Xinyu
    Liu, Shengnan
    Wang, Wenjuan
    Wang, Qiong
    Liu, Jianbiao
    Chen, Dezhan
    MOLECULAR CATALYSIS, 2021, 515
  • [10] Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles
    Marcum, Justin S.
    Roberts, Courtney C.
    Manan, Rajith S.
    Cervarich, Tia N.
    Meek, Simon J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (44) : 15580 - 15583