Gold-Catalyzed Tandem Cycloisomerization-Halogenation of Chiral Homopropargyl Sulfonamides

被引：21
|
作者：
Shu, Chao [1 ,2 ]
Li, Long [1 ,2 ]
Shen, Cang-Hai [1 ,2 ]
Ruan, Peng-Peng [1 ,2 ]
Liu, Chao-Yue [1 ,2 ]
Ye, Long-Wu [1 ,2 ,3 ]
机构：
[1] Xiamen Univ, Coll Chem & Chem Engn, State Key Lab Phys Chem Solid Surfaces, Xiamen 361005, Fujian, Peoples R China
[2] Xiamen Univ, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Fujian, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 07期
基金：
中国国家自然科学基金;
关键词：
cycloisomerization; gold; halogenation; heterocycles; homogeneous catalysis; EFFICIENT SYNTHESIS; INTERMOLECULAR OXIDATION; REGIOSELECTIVE SYNTHESIS; TERT-BUTANESULFINAMIDE; ASYMMETRIC-SYNTHESIS; ORGANOGOLD COMPOUNDS; PRACTICAL SYNTHESIS; PROPARGYLIC AMIDES; ALKYNES; DERIVATIVES;
D O I：
10.1002/chem.201503891
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Two new gold-catalyzed tandem cycloisomerization-halogenation reactions of chiral homopropargyl sulfonamides have been developed. Various enantioenriched 3,3-diiodopyrrolidin-2-ols and 3-fluoropyrrolidin-2-ols were obtained in moderate-to-good yields with excellent enantio- and diastereoselectivity.
引用
收藏
页码：2282 / 2290
页数：9
相关论文
共 50 条
  • [11] Efficient and practical synthesis of enantioenriched 2,3-dihydropyrroles through gold-catalyzed anti-Markovnikov hydroamination of chiral homopropargyl sulfonamides
    Yu, Yong-Fei
    Shu, Chao
    Zhou, Bo
    Li, Jian-Qiao
    Zhou, Jin-Mei
    Ye, Long-Wu
    CHEMICAL COMMUNICATIONS, 2015, 51 (11) : 2126 - 2129
  • [12] Gold-catalyzed cycloisomerization of siloxy enynes to cyclohexadienes
    Zhang, LM
    Kozmin, SA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (38) : 11806 - 11807
  • [13] New pathways in the gold-catalyzed cycloisomerization of furanynes
    Hashmi, A. Stephen K.
    PURE AND APPLIED CHEMISTRY, 2010, 82 (07) : 1517 - 1528
  • [14] Mechanism of Gold-Catalyzed Cycloisomerization of Enynyl Esters
    Correa, Andrea
    Cavallo, Luigi
    GREEN METATHESIS CHEMISTRY: GREAT CHALLENGES IN SYNTHESIS, CATALYSIS AND NANOTECHNOLOGY, 2010, : 293 - 303
  • [15] Gold-Catalyzed Cycloisomerization of Sulfur Ylides to Dihydrobenzothiepines
    Knittl-Frank, Christian
    Saridakis, Iakovos
    Stephens, Thomas
    Gomes, Rafael
    Neuhaus, James
    Misale, Antonio
    Oost, Rik
    Oppedisano, Alberto
    Maulide, Nuno
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (48) : 10972 - 10975
  • [16] Carene terpenoids by gold-catalyzed cycloisomerization reactions
    Fürstner, A
    Hannen, P
    CHEMICAL COMMUNICATIONS, 2004, (22) : 2546 - 2547
  • [17] Gold-catalyzed cycloisomerization reactions of boronated enynes
    Lee, Jack Chang Hung
    Hall, Dennis G.
    TETRAHEDRON LETTERS, 2011, 52 (02) : 321 - 324
  • [18] Synthesis of difurylmethane derivatives via the gold-catalyzed tandem cycloisomerization/dimerization of epoxide alkynes
    Ji, Ke-Gong
    Shen, Yong-Wen
    Shu, Xing-Zhong
    Xiao, Hui-Quan
    Bian, Yong-Jiang
    Liang, Yong-Min
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) : 1275 - 1280
  • [19] Gold-catalyzed intermolecular hydroamination of allenes with sulfonamides
    Zhang, Chen
    Zhang, Shao-Qiao
    Cai, Hua-Jun
    Cui, Dong-Mei
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 1045 - 1050
  • [20] On the nature of the reactive intermediates in gold-catalyzed cycloisomerization reactions
    Fuerstner, Alois
    Morency, Louis
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (27) : 5030 - 5033
12345