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

被引:241
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
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共 30 条
  • [1] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid
    Akiyama, T
    Itoh, J
    Yokota, K
    Fuchibe, K
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1566 - 1568
  • [2] Stronger bronsted acids
    Akiyama, Takahiko
    [J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5744 - 5758
  • [3] Highly enantioselective copper(I)-fesulphos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides
    Cabrera, S
    Arrayás, RG
    Carretero, JC
    [J]. 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
    Chen, C
    Li, XD
    Schreiber, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) : 10174 - 10175
  • [5] Highly enantioselective organocatalytic Biginelli reaction
    Chen, Xiao-Hua
    Xu, Xiao-Ying
    Liu, Hua
    Cun, Lin-Feng
    Gong, Liu-Zhu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) : 14802 - 14803
  • [6] Intramolecular dipolar cycloaddition reactions of azomethine ylides
    Coldham, I
    Hufton, R
    [J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2765 - 2809
  • [7] Small-molecule H-bond donors in asymmetric catalysis
    Doyle, Abigail G.
    Jacobsen, Eric N.
    [J]. 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
    Guo, Qi-Xiang
    Liu, Hua
    Guo, Chang
    Luo, Shi-Wei
    Gu, Yi
    Gong, Liu-Zhu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (13) : 3790 - +