Cu(I)/DTBM-BIPHEP-catalyzed exo-selective 1,3-dipolar cycloaddition of azomethine ylides with cis-trifluorocrotonate for asymmetric construction of trifluoromethylated pyrrolidines

被引：51
|
作者：
Li, Qing-Hua [1 ]
Xue, Zhi-Yong [1 ]
Tao, Hai-Yan [1 ]
Wang, Chun-Jiang [1 ,2 ]
机构：
[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei Province, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
TETRAHEDRON LETTERS | 2012年 / 53卷 / 28期
关键词：
Asymmetric catalysis; Pyrrolidine; Trifluoromethyl group; 1,3-Dipolar cycloaddition; Stereoselectivity; ENANTIOSELECTIVE 3+2 CYCLOADDITION; ESTERS;
D O I：
10.1016/j.tetlet.2012.05.021
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A direct and facile access to highly substituted exo-pyrrolidines bearing a unique trifluoromethyl group is developed via Cu(I)/DTBM-BIPHEP-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with cis-4,4,4-trifluorocrotonate for the first time. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3650 / 3653
页数：4
相关论文
共 50 条
  • [1] exo-Selective construction of spiro-[butyrolactone-pyrrolidine] via 1,3-dipolar cycloaddition of azomethine ylides with α-methylene-γ-butyrolactone catalyzed by Cu(I)/DTBM-BIPHEP
    Li, Qing-Hua
    Liu, Tang-Lin
    Wei, Liang
    Zhou, Xiang
    Tao, Hai-Yan
    Wang, Chun-Jiang
    CHEMICAL COMMUNICATIONS, 2013, 49 (83) : 9642 - 9644
  • [2] Cu(i)-Catalyzed asymmetric exo-selective synthesis of substituted pyrrolidines via a 1,3-dipolar cycloaddition reaction
    Biswas, Rayhan G.
    Ray, Sumit K.
    Kannaujiya, Vinod K.
    Unhale, Rajshekhar A.
    Singh, Vinod K.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (21) : 4685 - 4690
  • [3] Asymmetric construction of trifluoromethylated pyrrolidines via Cu(I)-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with 4,4,4-trifluorocrotonates
    Li, Qing-Hua
    Tong, Min-Chao
    Li, Jun
    Tao, Hai-Yan
    Wang, Chun-Jiang
    CHEMICAL COMMUNICATIONS, 2011, 47 (39) : 11110 - 11112
  • [4] Asymmetric construction of fluorinated imidazolidines via Cu(I)-catalyzed exo′-selective 1,3-dipolar cycloaddition of azomethine ylides with fluorinated imines
    Li, Qing-Hua
    Wei, Liang
    Chen, Xuan
    Wang, Chun-Jiang
    CHEMICAL COMMUNICATIONS, 2013, 49 (56) : 6277 - 6279
  • [5] exo-Selective asymmetric 1,3-dipolar cycloaddition of azomethine ylides with alkylidene malonates catalyzed by AgOAc/TF-BiphamPhos
    Xue, Zhi-Yong
    Liu, Tang-Lin
    Lu, Zhou
    Huang, He
    Tao, Hai-Yan
    Wang, Chun-Jiang
    CHEMICAL COMMUNICATIONS, 2010, 46 (10) : 1727 - 1729
  • [6] Chiral Trifluoromethylated Pyrrolidines via Cu-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition
    Cheng, Xiang
    Yan, Dingce
    Dong, Xiu-Qin
    Wang, Chun-Jiang
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (10) : 1567 - 1570
  • [7] Copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of 1,3-enynes and azomethine ylides
    Bo-Ran Wang
    Yan-Bo Li
    Qi Zhang
    Dingding Gao
    Ping Tian
    Qinghua Li
    Liang Yin
    Nature Communications, 14
  • [8] Copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of 1,3-enynes and azomethine ylides
    Wang, Bo-Ran
    Li, Yan-Bo
    Zhang, Qi
    Gao, Dingding
    Tian, Ping
    Li, Qinghua
    Yin, Liang
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [9] Catalytic asymmetric construction of Spiro pyrrolidines with contiguous quaternary centers via 1,3-dipolar cycloaddition of azomethine ylides
    Liu, Tanglin
    Li, Qinghua
    He, Zhaolin
    Zhang, Jiawei
    Wang, Chunjiang
    CHINESE JOURNAL OF CATALYSIS, 2015, 36 (01) : 68 - 77
  • [10] Catalytic asymmetric construction of spiropyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides
    Fang, Xin
    Wang, Chun-Jiang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (15) : 2591 - 2601
12345