Chromium-Catalyzed Asymmetric Dearomatization Addition Reactions of Halomethyl Heteroarenes

被引:34
作者
Tian, Qingshan [1 ]
Bai, Jing [1 ]
Chen, Bin [1 ]
Zhang, Guozhu [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
关键词
NOZAKI-HIYAMA ALLYLATION; TRIDENTATE BIS(OXAZOLINYL)CARBAZOLE LIGAND; ENANTIOSELECTIVE SYNTHESIS; NUCLEOPHILIC DEAROMATIZATION; ARYLATIVE DEAROMATIZATION; NAPHTHALENE DERIVATIVES; BIS(OXAZOLINE) LIGANDS; CARBONYL ADDITION; COUPLING REACTION; KISHI REACTION;
D O I
10.1021/acs.orglett.6b00559
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first asymmetric dearomatization addition reaction of halomethyl arenes including benzofuran and benzothiophene was enabled by chromium catalysis. A variety of aldehydes served as suitable electrophiles under mild reaction conditions. Molecular complexities are quickly increased in a highly diastereo- and enantioselective manner.
引用
收藏
页码:1828 / 1831
页数:4
相关论文
共 59 条
  • [1] Synthetic variations based on low-valent chromium:: new developments
    Avalos, M
    Babiano, R
    Cintas, P
    Jiménez, JL
    Palacios, JC
    [J]. CHEMICAL SOCIETY REVIEWS, 1999, 28 (03) : 169 - 177
  • [2] Bandini M, 1999, ANGEW CHEM INT EDIT, V38, P3357, DOI 10.1002/(SICI)1521-3773(19991115)38:22<3357::AID-ANIE3357>3.0.CO
  • [3] 2-W
  • [4] Facile allylative dearomatization catalyzed by palladium
    Bao, M
    Nakamura, H
    Yamamoto, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (04) : 759 - 760
  • [5] NI(II)/CR(II)-MEDIATED COUPLING REACTION - AN ASYMMETRIC PROCESS
    CHEN, CP
    TAGAMI, K
    KISHI, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) : 5386 - 5387
  • [6] Enantioselective Synthesis of α-exo-Methylene γ-Butyrolactones via Chromium Catalysis
    Chen, Weiqiang
    Yang, Qin
    Zhou, Tian
    Tian, Qingshan
    Zhang, Guozhu
    [J]. ORGANIC LETTERS, 2015, 17 (21) : 5236 - 5239
  • [7] THE META PHOTOCYCLOADDITION OF ARENES TO ALKENES
    CORNELISSE, J
    [J]. CHEMICAL REVIEWS, 1993, 93 (02) : 615 - 669
  • [8] The Synthesis of a New Class of Chiral Pincer Ligands and Their Applications in Enantioselective Catalytic Fluorinations and the Nozaki-Hiyama-Kishi Reaction
    Deng, Qing-Hai
    Wadepohl, Hubert
    Gade, Lutz H.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (52) : 14922 - 14928
  • [9] 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
  • [10] Enantioselective Palladium-Catalyzed Dearomative Cyclization for the Efficient Synthesis of Terpenes and Steroids
    Du, Kang
    Guo, Pan
    Chen, Yuan
    Cao, Zhen
    Wang, Zheng
    Tang, Wenjun
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (10) : 3033 - 3037