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
  • [31] Platinum- and gold-catalyzed cycloisomerization reactions of hydroxylated enynes
    Mamane, V
    Gress, T
    Krause, H
    Fürstner, A
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) : 8654 - 8655
  • [32] Golden times for allenes:: Gold-catalyzed cycloisomerization of β-hydroxyallenes to dihydropyrans
    Gockel, Birgit
    Krause, Norbert
    ORGANIC LETTERS, 2006, 8 (20) : 4485 - 4488
  • [33] Extrapolation of the gold-catalyzed cycloisomerization to the palladium-catalyzed cross-coupling/cycloisomerization of acetylenic alcohols for the synthesis of polysubstituted furans: Scope and application to tandem processes
    Praveen, Chandrasekar
    Perumal, Paramasivan T.
    CHINESE JOURNAL OF CATALYSIS, 2016, 37 (02) : 288 - 299
  • [34] Stereospecific access to bridged[n.2.1]skeletons through gold-catalyzed tandem reaction of indolyl homopropargyl amides
    Tong-De Tan
    Xin-Qi Zhu
    Mei Jia
    Yongjia Lin
    Jun Cheng
    Yuanzhi Xia
    Long-Wu Ye
    ChineseChemicalLetters, 2020, 31 (05) : 1309 - 1312
  • [35] Stereospecific access to bridged [n.2.1] skeletons through gold-catalyzed tandem reaction of indolyl homopropargyl amides
    Tan, Tong-De
    Zhu, Xin-Qi
    Jia, Mei
    Lin, Yongjia
    Cheng, Jun
    Xia, Yuanzhi
    Ye, Long-Wu
    CHINESE CHEMICAL LETTERS, 2020, 31 (05) : 1309 - 1312
  • [36] Bifunctional Biphenyl-2-ylphosphine Ligand Enables Tandem Gold-Catalyzed Propargylation of Aldehyde and Unexpected Cycloisomerization
    Li, Ting
    Zhang, Liming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (50) : 17439 - 17443
  • [37] Bifunctional Biphenyl-2-ylphosphine Ligand Enables Tandem Gold-Catalyzed Propargylation of Aldehyde and Unexpected Cycloisomerization
    Zhang, Liming (zhang@chem.ucsb.edu), 2018, American Chemical Society (140)
  • [38] Gold-Catalyzed Tandem Reactions of Methylenecyclopropanes and Vinylidenecyclopropanes
    Zhang, Di-Han
    Tang, Xiang-Ying
    Shi, Min
    ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (03) : 913 - 924
  • [39] DFT Studies on Gold-Catalyzed Cycloisomerization of 1,5-Enynes
    Fan, Ting
    Chen, Xihan
    Sun, Jianwei
    Lin, Zhenyang
    ORGANOMETALLICS, 2012, 31 (11) : 4221 - 4227
  • [40] Gold-Catalyzed Approach to Multisubstituted Fulvenes via Cycloisomerization of Furan/Ynes
    Chen, Yifeng
    Liu, Yuanhong
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (13): : 5274 - 5282
12345