CuII-catalysed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with a chiral ferrocene-derived P,N-ligand

被引:9
|
作者
Bdiri, Bilel [1 ]
Dai, Li [2 ]
Zhou, Zhi-Ming [1 ,3 ]
机构
[1] Beijing Inst Technol, Sch Chem Engn & Environm, R&D Ctr Pharmaceut, 5th Zhongguancun South St, Beijing 100081, Peoples R China
[2] Chinese Acad Sci, Inst Proc Engn, 1 North 2nd St, Beijing 100190, Peoples R China
[3] Beijing Inst Technol, State Key Lab Explos Sci & Technol, 5th Zhongguancun South St, Beijing 100081, Peoples R China
关键词
Pyrrolidine; Enantioselectivity; 1,3-Dipolar cycloaddition; Ferrocene ligand; LIGANDS; PROGRESS;
D O I
10.1016/j.tetlet.2017.05.044
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A ferrocene-derived P,N-heterodonor ligand was effectively used in a Cu(OAc)2 center dot H2O-catalysed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with maleate derivatives, affording cycloadducts with high yields (up to 96%), diastereoselectivities (>99 dr), and enantioselectivities (up to 99% ee). (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2475 / 2481
页数:7
相关论文
共 50 条
  • [21] 1,3-Dipolar cycloaddition reactions of azomethine ylides and alkynes
    Anna V. Gulevskaya
    Julia I. Nelina-Nemtseva
    Chemistry of Heterocyclic Compounds, 2018, 54 : 1084 - 1107
  • [22] CuI-fesulphos complexes:: efficient chiral catalysts for asymmetric 1,3-dipolar cycloaddition of azomethine ylides
    Cabrera, Silvia
    Arrayas, Ramon Gomez
    Martin-Matute, Belen
    Cossio, Fernando P.
    Carretero, Juan C.
    TETRAHEDRON, 2007, 63 (28) : 6587 - 6602
  • [23] Asymmetric Organocatalytic 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-Substituted Cyclic Enones
    Zhong, Han
    Zhang, Xiao-Yi
    Yao, Yong-Mou
    Chen, Wen-Ming
    Wang, Wei
    Tian, Xu
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (14): : 9721 - 9732
  • [24] STUDY OF THE ASYMMETRIC INDUCTION OF THE 1,3-DIPOLAR CYCLOADDITION OF CHIRAL AZOMETHINE YLIDES WITH UNACTIVATED DOUBLE-BONDS
    NEGRON, G
    ROUSSI, G
    ZHANG, JD
    HETEROCYCLES, 1992, 34 (02) : 293 - 301
  • [25] 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
  • [26] A convenient procedure for the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides and alkenes
    Alemparte, C
    Blay, G
    Jorgensen, KA
    ORGANIC LETTERS, 2005, 7 (21) : 4569 - 4572
  • [27] A facile synthesis of ferrocene grafted N-methyl-spiropyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides
    Sureshbabu, A. R.
    Raghunathan, R.
    Satiskumar, B. K.
    TETRAHEDRON LETTERS, 2009, 50 (23) : 2818 - 2821
  • [28] ASYMMETRIC CONTROL OF 1,3-DIPOLAR CYCLOADDITION REACTIONS WITH AZOMETHINE YLIDES BY MEANS OF PROLINE ESTERS AS CHIRAL AUXILIARY GROUPS
    WALDMANN, H
    BLASER, E
    JANSEN, M
    LETSCHERT, HP
    CHEMISTRY-A EUROPEAN JOURNAL, 1995, 1 (02) : 150 - 154
  • [29] 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
  • [30] Alkenyl Arenes as Dipolarophiles in Catalytic Asymmetric 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides
    Pascual-Escudero, Ana
    de Cozar, Abel
    Cossio, Fernando P.
    Adrio, Javier
    Carretero, Juan C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (49) : 15334 - 15338