Highly Enantioselective Cu-Catalyzed Conjugate Addition-Elimination of Activated Allylic Acetates with Glycine Derivatives

被引:44
作者
Chen, Chun-Gen [1 ]
Hou, Xue-Long [1 ]
Pu, Lin [2 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[2] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA
基金
中国国家自然科学基金;
关键词
ALPHA-AMINO-ACIDS; PHASE-TRANSFER CATALYSIS; BAYLIS-HILLMAN ACETATES; ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION; QUATERNARY AMMONIUM-SALTS; CHIRAL CALCIUM COMPLEXES; AZOMETHINE YLIDES; SCHIFF-BASE; KINETIC RESOLUTION; GAMMA-BUTENOLIDES;
D O I
10.1021/ol900439h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of a glycinate Schiff base with the activated alkyl- and aryl-substituted allylic acetates afforded 4-alkylidenylglutamic acid derivatives in high yields and high enantioselectivities by using Cu/P,N-FcPhox as the catalyst.
引用
收藏
页码:2073 / 2075
页数:3
相关论文
共 50 条
  • [21] Powerful chiral phase-transfer catalysts for the asymmetric synthesis of α-alkyl- and α,α,-dialkyl-α-amino acids
    Kitamra, M
    Shirakawa, S
    Maruoka, K
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (10) : 1549 - 1551
  • [22] Calcium-catalyzed diastereo- and enantioselective 1,4-addition of glycine derivatives to α,β-unsaturated esters
    Kobayashi, Shu
    Tsubogo, Tetsu
    Saito, Susumu
    Yamashita, Yasuhiro
    [J]. ORGANIC LETTERS, 2008, 10 (05) : 807 - 809
  • [23] Highly enantioselective Ag(I)-catalyzed [3+2] cycloaddition of azomethine ylides
    Longmire, JM
    Wang, B
    Zhang, XM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) : 13400 - 13401
  • [24] Bis-sulfonyl ethylene as masked acetylene equivalent in catalytic asymmetric [3+2] cycloaddition of azomethine ylides
    Lopez-Perez, Ana
    Adrio, Javier
    Carretero, Juan C.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (31) : 10084 - +
  • [25] Glutamic acid analogues as potent dipeptidyl peptidase IV and 8 inhibitors
    Lu, IL
    Lee, SJ
    Tsu, H
    Wu, SY
    Kao, KH
    Chien, CH
    Chang, YY
    Chen, YS
    Cheng, JH
    Chang, CN
    Chen, TW
    Chang, SP
    Chen, X
    Jiaang, WT
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (13) : 3271 - 3275
  • [26] A new class of asymmetric phase-transfer catalysts derived from Cinchona alkaloids - Application in the enantioselective synthesis of alpha-amino acids
    Lygo, B
    Wainwright, PG
    [J]. TETRAHEDRON LETTERS, 1997, 38 (49) : 8595 - 8598
  • [27] Catalytic enantioselective 1,3-dipolar cycloaddition reactions of azomethine ylides and alkenes by using phosphoramidite-silver(I) complexes
    Najera, Carmen
    Retamosa, M. de Gracia
    Sansano, Jose M.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (32) : 6055 - 6058
  • [28] Catalytic asymmetric synthesis of α-amino acids
    Najera, Carmen
    Sansano, Jose M.
    [J]. CHEMICAL REVIEWS, 2007, 107 (11) : 4584 - 4671
  • [29] The enantioselective synthesis of α-amino acids by phase-transfer catalysis with achiral Schiff base esters
    O'Donnell, MJ
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) : 506 - 517
  • [30] exo- and enantioselective cycloaddition of azomethine ylides generated from N-alkylidene glycine esters using chiral phosphine-copper complexes
    Oderaotoshi, Y
    Cheng, WJ
    Fujitomi, S
    Kasano, Y
    Minakata, S
    Komatsu, M
    [J]. ORGANIC LETTERS, 2003, 5 (26) : 5043 - 5046