Cu(i)-Catalyzed asymmetric intramolecular addition of aryl pinacolboronic esters to unactivated ketones: enantioselective synthesis of 2,3-dihydrobenzofuran-3-ol derivatives

被引:17
作者
Ni, Chunjie [1 ,2 ]
Gao, Jihui [1 ]
Fang, Xianjie [1 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
[2] Yancheng Teachers Univ, Sch Pharm, Yancheng 224051, Peoples R China
基金
中国博士后科学基金;
关键词
RHODIUM-CATALYZED ADDITION; CROSS-COUPLING REACTIONS; ARYLBORONIC ACIDS; PHOSPHORUS LIGANDS; ALPHA-DIKETONES; SUZUKI-MIYAURA; NAPHTHOQUINONES; 1,2-ADDITION; DIARYLATION; ALCOHOLS;
D O I
10.1039/c9cc09653a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An (S,S)-QuinoxP*-supported Cu(i) catalyst has been disclosed for highly enantioselective intramolecular addition of aryl pinacolboronic esters to unactivated ketones under mild reaction conditions. This protocol showcases a broad substrate tolerance and allows access to various chiral 2,3-dihydrobenzofuran-3-ol derivatives in generally good yields with excellent enantioselectivities.
引用
收藏
页码:2654 / 2657
页数:4
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共 49 条
  • [1] Chiral Allene-Containing Phosphines in Asymmetric Catalysis
    Cai, Feng
    Pu, Xiaotao
    Qi, Xiangbing
    Lynch, Vincent
    Radha, Akella
    Ready, Joseph M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (45) : 18066 - 18069
  • [2] Enantioselective Nickel-Catalyzed Mizoroki Heck Cyclizations To Generate Quaternary Stereocenters
    Desrosiers, Jean-Nicolas
    Wen, Jialin
    Tcyrulnikov, Sergei
    Biswas, Soumik
    Qu, Bo
    Hie, Liana
    Kurouski, Dmitry
    Wu, Ling
    Grinberg, Nelu
    Haddad, Nizar
    Busacca, Carl A.
    Yee, Nathan K.
    Song, Jinhua J.
    Garg, Neil K.
    Zhang, Xumu
    Kozlowski, Marisa C.
    Senanayake, Chris H.
    [J]. ORGANIC LETTERS, 2017, 19 (13) : 3338 - 3341
  • [3] Enantioselective rhodium-catalyzed addition of arylboronic acids to α-ketoesters
    Duan, Hai-Feng
    Xie, Jian-Hua
    Qiao, Xiang-Chen
    Wang, Li-Xin
    Zhou, Qi-Lin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (23) : 4351 - 4353
  • [4] Synthesis of Chiral α-Aminosilanes through Palladium-Catalyzed Asymmetric Hydrogenation of Silylimines
    Fan, Dongyang
    Liu, Yang
    Jia, Jia
    Zhang, Zhenfeng
    Liu, Yangang
    Zhang, Wanbin
    [J]. ORGANIC LETTERS, 2019, 21 (04) : 1042 - 1045
  • [5] Rh(I)-Catalyzed Asymmetric 1,2-Addition to α-Diketones with Chiral Sulfur-Alkene Hybrid Ligands
    Feng, Xiangqing
    Hie, Yanzhao
    Yang, Jing
    Du, Haifeng
    [J]. ORGANIC LETTERS, 2012, 14 (02) : 624 - 627
  • [6] Chiral Monophosphorus Ligands for Asymmetric Catalytic Reactions
    Fu, Wenzhen
    Tang, Wenjun
    [J]. ACS CATALYSIS, 2016, 6 (08): : 4814 - 4858
  • [7] Rh(I)-catalyzed enantioselective intramolecular hydroarylation of unactivated ketones with aryl pinacolboronic esters
    Gallego, Gary M.
    Sarpong, Richmond
    [J]. CHEMICAL SCIENCE, 2012, 3 (04) : 1338 - 1342
  • [8] Rh(I)-catalyzed asymmetric addition of arylboronic acids to NH isatins
    Gui, Jiangyang
    Chen, Guihua
    Cao, Peng
    Liao, Jian
    [J]. TETRAHEDRON-ASYMMETRY, 2012, 23 (08) : 554 - 563
  • [9] ALKALOIDS AND COUMARINS OF HERACLEUM-WALLICHII
    GUPTA, BD
    BANERJEE, SK
    HANDA, KL
    [J]. PHYTOCHEMISTRY, 1976, 15 (04) : 576 - 576
  • [10] Catalytic enantioselective organozinc addition toward optically active tertiary alcohol synthesis
    Hatano, Manabu
    Ishihara, Kazuaki
    [J]. CHEMICAL RECORD, 2008, 8 (03) : 143 - 155