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 31 条
[1]   CHIRAL CO(II) AND MN(II) CATALYSTS FOR THE 1,3-DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE YLIDES DERIVED FROM ARYLIDENE IMINES OF GLYCINE [J].
ALLWAY, P ;
GRIGG, R .
TETRAHEDRON LETTERS, 1991, 32 (41) :5817-5820
[2]   N-tert-Butanesulfinyl imine and aromatic tertiary amide derived non-biaryl atropisomers as chiral ligands for silver-catalyzed endo-selective [3+2] cycloaddition of azomethine ylides with maleimides [J].
Bai, Xing-Feng ;
Zhang, Jin ;
Xia, Chun-Gu ;
Xu, Jian-Xing ;
Xu, Li-Wen .
TETRAHEDRON, 2016, 72 (21) :2690-2699
[3]   Asymmetric Copper-Catalyzed Azide-Alkyne Cycloadditions [J].
Brittain, William D. G. ;
Buckley, Benjamin R. ;
Fossey, John S. .
ACS CATALYSIS, 2016, 6 (06) :3629-3636
[4]   Densely substituted unnatural L- and D-prolines as catalysts for highly enantioselective stereodivergent (3+2) cycloadditions and aldol reactions [J].
Conde, Egoitz ;
Bello, Davide ;
de Cozar, Abel ;
Sanchez, Mirian ;
Vazquez, Miguel A. ;
Cossio, Fernando P. .
CHEMICAL SCIENCE, 2012, 3 (05) :1486-1491
[5]   A CuII-N,P Oxazolinylferrocene Ligand Complex for the Asymmetric [3+2] 1,3-Dipolar Cycloaddition of Azomethine Ylide with Malonates [J].
Dai, Li ;
Xu, Di ;
Tang, Li-Wei ;
Zhou, Zhi-Ming .
CHEMCATCHEM, 2015, 7 (07) :1078-1082
[6]   Highly enantioselective asymmetric 1,3-dipolar cycloaddition of azomethine ylide catalyzed by a copper(I)/ClickFerrophos complex [J].
Fukuzawa, Shin-ichi ;
Oki, Hiroshi .
ORGANIC LETTERS, 2008, 10 (09) :1747-1750
[7]   Cu(I)-catalyzed highly exo-selective and enantioselective [3+2] cycloaddition of azomethine ylides with acrylates [J].
Gao, WZ ;
Zhang, XM ;
Raghunath, M .
ORGANIC LETTERS, 2005, 7 (19) :4241-4244
[8]   N-Acyliminoimidazolium Ylides as Precursors to Anionic N-Heterocyclic Carbene Ligands: Control of Topology and Reactivity [J].
Guernon, Hannah ;
Legault, Claude Y. .
ORGANOMETALLICS, 2013, 32 (06) :1988-1994
[9]   Chiral ferrocenyl P,S-ligands for highly efficient copper-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides [J].
Han, Fu-Zhong ;
Yu, Sai-Bo ;
Zhang, Cheng ;
Hu, Xiang -Ping .
TETRAHEDRON, 2016, 72 (21) :2616-2622
[10]   Recent Advances of Catalytic Asymmetric 1,3-Dipolar Cycloadditions [J].
Hashimoto, Takuya ;
Maruoka, Keiji .
CHEMICAL REVIEWS, 2015, 115 (11) :5366-5412