Chiral Iminophosphorane Organocatalyzed Asymmetric Sulfenylation of 3-Substituted Oxindoles: Substrate-Interrelated Enantioselectivities

被引：15
|
作者：
Gao, Xing [1 ,2 ,3 ]
Han, Jianwei [3 ]
Wang, Limin [1 ,2 ]
机构：
[1] East China Univ Sci & Technol, Key Lab Adv Mat, 130 Mei Long Rd, Shanghai 200237, Peoples R China
[2] East China Univ Sci & Technol, Inst Fine Chem, 130 Mei Long Rd, Shanghai 200237, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, 345 Ling Ling Rd, Shanghai 200032, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2016年 / 48卷 / 16期
关键词：
organocatalysis; phosphazene; iminophosphorane; sulfenylation; oxindole; BETA-KETO-ESTERS; ALPHA-AMINATION; SUBSTITUTED OXINDOLES; MOLECULAR-OXYGEN; FLUORINATION; HYDROXYLATION; ALDEHYDES; 3-HYDROXY-2-OXINDOLES; SPIROOXINDOLES; CHLORINATION;
D O I：
10.1055/s-0035-1560435
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Catalytic asymmetric sulfenylation of 3-substituted oxindoles has been developed through efficient catalysis by tartaric acid derived chiral iminophosphoranes. With N-(phenylthio)phthalimide as the sulfur source, a wide range of optically active 3-phenylthiooxindoles were obtained in excellent yields (90-99%) and good enantiomeric excess (up to 90% ee). Interestingly, 3-aryl and 3-methyl substituted oxindoles afforded sulfenylated products in S-configuration, whereas substituted oxindoles with 3-arylidene or 3-isobutyl substituents gave the corresponding R-configured sulfenylated products.
引用
收藏
页码：2603 / 2611
页数：9
相关论文
共 50 条
  • [31] Synthesis and Application of 3-Substituted (S)-BINOL as Chiral Ligands for the Asymmetric Ethylation of Aldehydes
    Zhang, Zhi-Guang
    Dong, Zhi-Bing
    Li, Jin-Shan
    CHIRALITY, 2010, 22 (09) : 820 - 826
  • [32] Scandium-Catalyzed Asymmetric 1,6-Addition of 3-Substituted Oxindoles to Linear Dienyl Ketones
    Wang, Zhen
    Kang, Tengfei
    Yao, Qian
    Ji, Jie
    Liu, Xiaohua
    Lin, Lili
    Feng, Xiaoming
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (21) : 7709 - 7712
  • [33] A facile synthesis and asymmetric catalytic activity of new 3-substituted chiral BINOL ligands
    Liu, Bing
    Fang, Cao
    Dong, Zhi-Bing
    Li, Jin-Shan
    APPLIED ORGANOMETALLIC CHEMISTRY, 2008, 22 (01) : 55 - 58
  • [34] Highly enantioselective synthesis of chiral 3-substituted indolines by catalytic asymmetric hydrogenation of indoles
    Kuwano, R
    Kaneda, K
    Ito, T
    Sato, K
    Kurokawa, T
    Ito, Y
    ORGANIC LETTERS, 2004, 6 (13) : 2213 - 2215
  • [35] Synthesis of chiral 3-substituted 3-amino-2-oxindoles through enantioselective catalytic nucleophilic additions to isatin imines
    Pellissier, Helene
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 : 1349 - 1369
  • [36] Synthesis of Chiral 3-Substituted Benzoquinone Compounds Through Asymmetric Catalytic Tandem Reaction with Chiral Phosphoramide as Catalyst
    Guo Qingjun
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2019, 40 (10): : 2104 - 2110
  • [37] Chiral phosphine-catalyzed asymmetric allylic alkylation of 3-substituted benzofuran-2(3H)-ones or oxindoles with Morita-Baylis-Hillman carbonates
    Wang, De
    Yang, Yuan-Liang
    Jiang, Jia-Jun
    Shi, Min
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (35) : 7158 - 7166
  • [38] Asymmetric synthesis of 3-substituted unsaturated prolines from chiral sulfoximine substituted allyl titanium(IV) complexes
    Tiwari, SK
    Schneider, A
    Koep, S
    Gais, HJ
    TETRAHEDRON LETTERS, 2004, 45 (45) : 8343 - 8346
  • [39] Enantioselective direct Mannich reactions of 3-substituted oxindoles catalyzed by chiral phosphine via dual-reagent catalysis
    Jin, Qiaowen
    Zheng, Changwu
    Zhao, Gang
    Zou, Gang
    TETRAHEDRON, 2018, 74 (30) : 4134 - 4144
  • [40] Recent Progress in the Construction of Chiral 3-Substituted Indoles by Asymmetric Friedel-Crafts Reactions
    Liu Tiantian
    Duan Xinhong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (11) : 3695 - 3712
12345