Noyori's Ts-DPEN Ligand: Simple yet Effective Catalyst for the Highly Enantioselective Michael Addition of Acetone to Nitroalkenes

被引：51
作者：
Peng, Lin [1 ,2 ]
Xu, Xiao-Ying [1 ]
Wang, Liang-Liang [1 ,2 ]
Huang, Jun [1 ,2 ]
Bai, Jian-Fei [1 ,2 ]
Huang, Qing-Chun [1 ]
Wang, Li-Xin [1 ]
机构：
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Grad Univ, Beijing 10039, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 10期
基金：
中国国家自然科学基金;
关键词：
Organocatalysis; Michael addition; Asymmetric synthesis; Amines; DIRECT CONJUGATE ADDITION; ALDOL REACTIONS; BIFUNCTIONAL ORGANOCATALYSTS; ASYMMETRIC ORGANOCATALYSIS; EFFICIENT ORGANOCATALYSTS; 1,4-ADDITION REACTIONS; PYRROLIDINE-THIOUREA; AROMATIC KETONES; CYCLIC-KETONES; ALDEHYDES;
D O I：
10.1002/ejoc.200901509
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Highly enantioselective Michael addition of acetone to a variety of nitroalkenes promoted by simple chiral primary amine bifunctional catalysts (e.g., Noyori's Ts-DPEN ligand) together with terephthalic acid in excellent yields (84-99%) and enantioselectivities (93-98 % ee) is reported.
引用
收藏
页码：1849 / 1853
页数：5
相关论文
共 84 条
  • [1] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene
    Alexakis, A
    Andrey, O
    [J]. ORGANIC LETTERS, 2002, 4 (21) : 3611 - 3614
  • [2] Theory of asymmetric organocatalysis of aldol and related reactions: Rationalizations and predictions
    Allemann, C
    Gordillo, R
    Clemente, FR
    Cheong, PHY
    Houk, KN
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) : 558 - 569
  • [3] Organocatalytic asymmetric conjugate additions
    Almasi, Diana
    Alonso, Diego A.
    Najera, Carmen
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (03) : 299 - 365
  • [4] The use of N-alkyl-2,2′-bipyrrolidine derivatives as organocatalysts for the asymmetric Michael addition of ketones and aldehydes to nitroolefins
    Andrey, O
    Alexakis, A
    Tomassini, A
    Bernardinelli, G
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1147 - 1168
  • [5] The origin of stereoselectivity in proline-catalyzed intramolecular aldol reactions
    Bahmanyar, S
    Houk, KN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) : 12911 - 12912
  • [6] Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results
    Ballini, R
    Bosica, G
    Fiorini, D
    Palmieri, A
    Petrini, M
    [J]. CHEMICAL REVIEWS, 2005, 105 (03) : 933 - 971
  • [7] Chiral piperazines as efficient catalysts for the asymmetric Michael addition of aldehydes to nitroalkenes
    Barros, Maria Teresa
    Phillips, Ana Maria Faisca
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (01) : 178 - 185
  • [8] Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
  • [9] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors
    Betancort, JM
    Barbas, CF
    [J]. ORGANIC LETTERS, 2001, 3 (23) : 3737 - 3740
  • [10] Pyrrolidine-thiourea as a bifunctional organocatalyst: Highly enantioselective Michael addition of cyclohexanone to nitroolefins
    Cao, Chun-Li
    Ye, Meng-Chun
    Sun, Xiu-Li
    Tang, Yong
    [J]. ORGANIC LETTERS, 2006, 8 (14) : 2901 - 2904
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