Organocatalytic asymmetric chlorinative dearomatization of naphthols

被引:105
作者
Yin, Qin [1 ]
Wang, Shou-Guo [1 ]
Liang, Xiao-Wei [1 ]
Gao, De-Wei [1 ]
Zheng, Jun [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
ENANTIOSELECTIVE SYNTHESIS; OXIDATIVE DEAROMATIZATION; ALLYLIC DEAROMATIZATION; PHENOL DEAROMATIZATION; MICHAEL REACTION; DESYMMETRIZATION; CYCLOHEXADIENONES; SPIROLACTONIZATION; CHLOROCYCLIZATION; CONSTRUCTION;
D O I
10.1039/c5sc00494b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An organocatalytic asymmetric chlorinative dearomatization of naphthols was realized for the first time, providing chiral naphthalenones with a Cl-containing all-substituted stereocenter in excellent yields and enantioselectivity (up to 97% yield and 96% ee). The reaction features mild reaction conditions, good tolerance of diverse functional groups and simple reaction operation.
引用
收藏
页码:4179 / 4183
页数:5
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共 64 条
  • [1] Radical chain reactions of α-azido-β-keto esters with tributyltin hydride.: A novel entry to amides and lactams through regiospecific nitrogen insertion
    Benati, L
    Nanni, D
    Sangiorgi, C
    Spagnolo, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) : 7836 - 7841
  • [2] Chiral- Amine- Catalyzed Asymmetric Bromocyclization of Tryptamine Derivatives
    Cai, Quan
    Yin, Qin
    You, Shu-Li
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (04) : 408 - 411
  • [3] Current Methods for Asymmetric Halogenation of Olefins
    Castellanos, Alejandro
    Fletcher, Stephen P.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (21) : 5766 - 5776
  • [4] Enantioselective Halocyclization Reactions for the Synthesis of Chiral Cyclic Compounds
    Chen, Guofei
    Ma, Shengming
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (45) : 8306 - 8308
  • [5] Organocatalytic Asymmetric Halogenation/Semipinacol Rearrangement: Highly Efficient Synthesis of Chiral α-Oxa-Quaternary β-Haloketones
    Chen, Zhi-Min
    Zhang, Qing-Wei
    Chen, Zhi-Hua
    Li, Hui
    Tu, Yong-Qiang
    Zhang, Fu-Min
    Tian, Jin-Miao
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (23) : 8818 - 8821
  • [6] Recent advances in asymmetric intra- and intermolecular halofunctionalizations of alkenes
    Cheng, Yi An
    Yu, Wesley Zongrong
    Yeung, Ying-Yeung
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (15) : 2333 - 2343
  • [7] Enantioselective synthesis of hindered cyclic dialkyl ethers via catalytic oxa-Michael/Michael desymmetrization
    Corbett, Michael T.
    Johnson, Jeffrey S.
    [J]. CHEMICAL SCIENCE, 2013, 4 (07) : 2828 - 2832
  • [8] Catalytic, Asymmetric Halofunctionalization of Alkenes-A Critical Perspective
    Denmark, Scott E.
    Kuester, William E.
    Burk, Matthew T.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (44) : 10938 - 10953
  • [9] A chiral hypervalent iodine(III) reagent for enantioselective dearomatization of phenols
    Dohi, Toshifumi
    Maruyama, Akinobu
    Takenaga, Naoko
    Senami, Kento
    Minamitsuji, Yutaka
    Fujioka, Hiromichi
    Caemmerer, Simon B.
    Kita, Yasuyuki
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (20) : 3787 - 3790
  • [10] Asymmetric Dearomatizing Spirolactonization of Naphthols Catalyzed by Spirobiindane-Based Chiral Hypervalent Iodine Species
    Dohi, Toshifumi
    Takenaga, Naoko
    Nakae, Tomofumi
    Toyoda, Yosuke
    Yamasaki, Mikio
    Shiro, Motoo
    Fujioka, Hiromichi
    Maruyama, Akinobu
    Kita, Yasuyuki
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (11) : 4558 - 4566