Asymmetric organocatalytic three-component 1,3-dipolar cycloaddition: Control of stereochemistry via a chiral bronsted acid activated dipole

被引:243
作者
Chen, Xiao-Hua [1 ,2 ,3 ]
Zhang, Wen-Quan [1 ,2 ]
Gong, Liu-Zhu [1 ,2 ,3 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
[3] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
关键词
D O I
10.1021/ja801034e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Bronsted acid catalyzed three-component asymmetric 1,3-dipolar addition reaction between aldehydes, amino esters, and dipolarophiles by a new bisphosphoric acid, derived from the linked BINOL, furnished multiply substituted pyrrolidines in high yield with excellent enantioselectivities under mild conditions.
引用
收藏
页码:5652 / +
页数:3
相关论文
共 30 条
[1]   Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].
Akiyama, T ;
Itoh, J ;
Yokota, K ;
Fuchibe, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568
[2]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[3]   Highly enantioselective copper(I)-fesulphos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides [J].
Cabrera, S ;
Arrayás, RG ;
Carretero, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) :16394-16395
[4]   Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis [J].
Chen, C ;
Li, XD ;
Schreiber, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10174-10175
[5]   Highly enantioselective organocatalytic Biginelli reaction [J].
Chen, Xiao-Hua ;
Xu, Xiao-Ying ;
Liu, Hua ;
Cun, Lin-Feng ;
Gong, Liu-Zhu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) :14802-14803
[6]   Intramolecular dipolar cycloaddition reactions of azomethine ylides [J].
Coldham, I ;
Hufton, R .
CHEMICAL REVIEWS, 2005, 105 (07) :2765-2809
[7]   Small-molecule H-bond donors in asymmetric catalysis [J].
Doyle, Abigail G. ;
Jacobsen, Eric N. .
CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743
[8]  
Gothelf AS, 2002, ANGEW CHEM INT EDIT, V41, P4236, DOI 10.1002/1521-3773(20021115)41:22<4236::AID-ANIE4236>3.0.CO
[9]  
2-W
[10]   Chiral Bronsted acid-catalyzed direct asymmetric Mannich reaction [J].
Guo, Qi-Xiang ;
Liu, Hua ;
Guo, Chang ;
Luo, Shi-Wei ;
Gu, Yi ;
Gong, Liu-Zhu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (13) :3790-+