Highly enantioselective Michael-cyclization cascade promoted by synergistic asymmetric aminocatalysis and Lewis acid catalysis

被引:34
作者
Yu, Chenguang [1 ,2 ]
Zhang, Yinan [2 ]
Zhang, Shilei [2 ]
He, Jing [1 ]
Wang, Wei [2 ]
机构
[1] Beijing Inst Chem Technol, State Key Lab Chem Resources Engn, Beijing 100029, Peoples R China
[2] Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA
关键词
Cascade; Michael; Organocatalysis; Pd catalysis; TRANSITION-METAL CATALYSIS; DIPHENYLPROLINOL SILYL ETHER; ALPHA; BETA-UNSATURATED ALDEHYDES; ALDOL REACTIONS; BRONSTED ACID; ADDITION-REACTIONS; DOMINO REACTIONS; STEREOCENTERS; ALDER REACTIONS; GOLD CATALYSIS;
D O I
10.1016/j.tetlet.2010.01.096
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The novel dual cooperative asymmetric aminocatalysis and Lewis acid catalysis has been successfully developed for promoting cascade Michael-cyclization reaction with high enantio-, regio- and chemo-selectivity. The simple and practical process affords a one-pot approach to synthetically useful cyclopentenes. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1742 / 1744
页数:3
相关论文
共 67 条
[1]   Enantioselective One-Pot Organocatalytic Michael Addition/Gold-Catalyzed Tandem Acetalization/Cyclization [J].
Belot, Sebastien ;
Vogt, Kim A. ;
Besnard, Celine ;
Krause, Norbert ;
Alexakis, Alexandre .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (47) :8923-8926
[2]   Targeting Structural and Stereochemical Complexity by Organocascade Catalysis: Construction of Spirocyclic Oxindoles Having Multiple Stereocenters [J].
Bencivenni, Giorgio ;
Wu, Li-Yuan ;
Mazzanti, Andrea ;
Giannichi, Berardino ;
Pesciaioli, Fabio ;
Song, Mao-Ping ;
Bartoli, Giuseppe ;
Melchiorre, Paolo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (39) :7200-7203
[3]   Organocatalysis-after the gold rush [J].
Bertelsen, Soren ;
Jorgensen, Karl Anker .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2178-2189
[4]   Catalytic enantioselective synthesis of flavanones and chromanones [J].
Biddle, Margaret M. ;
Lin, Michael ;
Scheidt, Karl A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (13) :3830-+
[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]   Asymmetric Construction of Polycyclic Indoles through Olefin Cross-Metathesis/Intramolecular Friedel-Crafts Alkylation under Sequential Catalysis [J].
Cai, Quan ;
Zhao, Zhuo-An ;
You, Shu-Li .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (40) :7428-7431
[8]   A new approach for an organocatalytic multicomponent domino asymmetric reaction [J].
Carlone, Armando ;
Cabrera, Silvia ;
Marigo, Mauro ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) :1101-1104
[9]   Tandem metal- and organocatalysis in sequential hydroformylation and enantioselective aldol reactions [J].
Chercheja, Serghei ;
Eilbracht, Peter .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (11-12) :1897-1905
[10]   Amine-catalyzed cyclizations of tethered α,β-unsaturated carbonyl compounds [J].
de Figueiredo, Renata Marcia ;
Froehlich, Roland ;
Christmann, Mathias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (08) :1450-1453