The Marriage of Organocatalysis with Metal Catalysis: Access to Multisubstituted Chiral 2,5-Dihydropyrroles by Cascade Iminium/Enamine-Metal Cooperative Catalysis

被引:48
作者
Sun, Wangsheng [1 ]
Zhu, Gongming [1 ]
Hong, Liang [1 ]
Wang, Rui [1 ]
机构
[1] Lanzhou Univ, Key Lab Preclin Study New Drugs Gansu Prov, Sch Basic Med Sci, Inst Biochem & Mol Biol,Sch Life Sci, Lanzhou 730000, Peoples R China
关键词
aldehydes; cascade reaction; cooperative catalysis; organocatalysis; propargylamines; pyrrolines; FRIEDEL-CRAFTS ALKYLATION; ACTIVE THROMBIN INHIBITORS; TRANSITION-METAL; ALPHA; BETA-UNSATURATED ALDEHYDES; ENANTIOSELECTIVE SYNTHESIS; 3+2 CYCLOADDITION; GOLD CATALYSIS; MULTICOMPONENT REACTIONS; WATER; COMBINATION;
D O I
10.1002/chem.201103083
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Organocatalyst and metal cooperate: The integration of iminium catalysis and enamine-metal cooperative catalysis into a single process facilitates the rapid and controlled production of valuable chiral pyrrolines in excellent diastereo- and enantioselectivities (see scheme). Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:13958 / 13962
页数:5
相关论文
共 90 条
[1]  
[Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650
[2]  
[Anonymous], 2011, ANGEW CHEM, DOI DOI 10.1021/JA8045519
[3]  
Beller M., 2004, TRANSITION METALS OR
[4]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[5]   Organocatalyzed cyclizations of π-allylpalladium complexes:: A new method for the construction of five- and six-membered rings [J].
Bihelovic, Filip ;
Matovic, Radomir ;
Vulovic, Bojan ;
Saicic, Radomir N. .
ORGANIC LETTERS, 2007, 9 (24) :5063-5066
[6]   Direct carbocyclization of aldehydes with alkynes: Combining gold catalysis with aminocatalysis [J].
Binder, Jorg T. ;
Crone, Benedikt ;
Haug, Timm T. ;
Menz, Helge ;
Kirsch, Stefan F. .
ORGANIC LETTERS, 2008, 10 (05) :1025-1028
[7]  
Blackmond D.G., 2007, ANGEW CHEM, V119, P3872
[8]   Water in organocatalytic processes: Debunking the myths [J].
Blackmond, Donna G. ;
Armstrong, Alan ;
Coombe, Vyv ;
Wells, Andrew .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (21) :3798-3800
[9]  
Brogan A. P., 2006, ANGEW CHEM, V118, P8278
[10]   Enamine-based aldol organocatalysis in water: Are they really "all wet"? [J].
Brogan, Andrew P. ;
Dickerson, Tobin J. ;
Janda, Kim D. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (48) :8100-8102