Cu(I)-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with 2-Aryl-N-sulfonylaziridines as Alkylating Agents

被引：42
|
作者：
Ge, Chen [1 ]
Liu, Ren-Rong [1 ]
Gao, Jian-Rong [1 ]
Jia, Yi-Xia [1 ]
机构：
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 13期
基金：
中国国家自然科学基金;
关键词：
CARBON QUATERNARY STEREOCENTERS; RING-OPENING REACTIONS; MESO-EPOXIDES; LEWIS-ACID; ASYMMETRIC-SYNTHESIS; KINETIC RESOLUTION; CONSTRUCTION; AZIRIDINES; DERIVATIVES; PYRROLOINDOLINES;
D O I：
10.1021/acs.orglett.6b01317
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly enantioselective Friedel-Crafts alkylation of indoles with N-sulfonylaziridines as alkylating agents has been developed by utilizing the complex of Cu-(CH3CN)(4)BF4/(S)-Segphos as a catalyst. A range of optically active tryptamine derivatives are obtained in good to excellent yields and enantioselectivities (up to >99% ee) via a kinetic resolution process.
引用
收藏
页码：3122 / 3125
页数：4
相关论文
共 50 条
  • [21] Enantioselective Friedel-Crafts Reaction of Indoles with Trifluoroacetaldehyde Catalyzed by Cinchona Alkaloids
    Borkin, Dmitry A.
    Landge, Shainaz M.
    Toeroek, Bela
    CHIRALITY, 2011, 23 (08) : 612 - 616
  • [22] Enantioselective Friedel-Crafts alkylation reaction of indoles with α,β-unsaturated acyl phosphonates catalyzed by chiral phosphoric acid
    Bachu, Prabhakar
    Akiyama, Takahiko
    CHEMICAL COMMUNICATIONS, 2010, 46 (23) : 4112 - 4114
  • [23] Chriral Bis(oxazolidine) pyridine-Copper-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with Nitroalkenes
    Sato, Toru
    Arai, Takayoshi
    SYNLETT, 2014, 25 (03) : 349 - 354
  • [24] Enantioselective Friedel-Crafts Alkylation Reaction of Indoles with α-Trifluoromethylated β-Nitrostyrenes Catalyzed by Chiral BINOL Metal Phosphate
    Ibanez, Ignacio
    Kaneko, Mio
    Kamei, Yuto
    Tsutsumi, Ryosuke
    Yamanaka, Masahiro
    Akiyama, Takahiko
    ACS CATALYSIS, 2019, 9 (08) : 6903 - 6909
  • [25] Designing new α,β-unsaturated thioesters for the catalytic, enantioselective Friedel-Crafts alkylation of indoles
    Bandini, M
    Melloni, A
    Tommasi, S
    Umani-Ronchi, A
    HELVETICA CHIMICA ACTA, 2003, 86 (11) : 3753 - 3763
  • [26] An Efficient Enantioselective Method for Asymmetric Friedel-Crafts Alkylation of Indoles with α,β-Unsaturated Aldehydes
    Hong, Liang
    Wang, Lei
    Chen, Chao
    Zhang, Bangzhi
    Wang, Rui
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (05) : 772 - 778
  • [27] Squaramide-catalyzed enantioselective Friedel-Crafts reaction of indoles with imines
    Qian, Yong
    Ma, Gaoyuan
    Lv, Aifeng
    Zhu, Hai-Liang
    Zhao, Jing
    Rawal, Viresh H.
    CHEMICAL COMMUNICATIONS, 2010, 46 (17) : 3004 - 3006
  • [28] Copper-Catalyzed Enantioselective Friedel-Crafts Alkylation of Pyrrole with Isatins
    Li, Chong
    Guo, Fengfeng
    Xu, Kun
    Zhang, Sheng
    Hu, Yanbin
    Zha, Zhenggen
    Wang, Zhiyong
    ORGANIC LETTERS, 2014, 16 (12) : 3192 - 3195
  • [29] Enantioselective Friedel-Crafts reaction of indoles with arylidene malonates catalyzed by iPr-bisoxazoline-Cu(OTf)2
    Zhou, J
    Tang, Y
    CHEMICAL COMMUNICATIONS, 2004, (04) : 432 - 433
  • [30] Dy(OTf)3/Pybox-catalyzed enantioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated trifluoromethyl ketones
    Sasaki, Shigeru
    Yamauchi, Takayasu
    Higashiyama, Kimio
    TETRAHEDRON LETTERS, 2010, 51 (17) : 2326 - 2328
12345