Organocatalytic asymmetric Mannich reaction

被引:0
作者
Ma Jingjun [1 ]
Li Ning [1 ,2 ]
Wu Qiuhua [1 ]
Zhou Xin [1 ]
Zang Xiaohuan [1 ]
Wang Chun [1 ]
机构
[1] Agr Univ Hebei, Coll Sci, Hebei Key Lab Bioinorgan Chem, Baoding 071001, Peoples R China
[2] Agr Univ Hebei, Coll Food Sci & Technol, Baoding 071001, Peoples R China
关键词
organocatalysis; enantioselectivity; asymmetric Mannich reaction;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Organocatalytic asymmetric reaction is an increasingly active area in organic synthesis. Asymmetric Mannich reaction is a powerful tool for the synthesis of beta-amino-carbonyl compounds. The reported organocatalyst for asymmetric Mannich reaction includes proline derivatives, chiral phosphoric acids, chiral ( thio) urea derivatives, cinchona alkaloids etc. which can catalyze the asymmetric Mannich reaction with high catalytic activity and excellent enantioselectivity. The applications of various organocatalysts in asymmetric Mannich reaction are reviewed in this paper. The reaction mechanism, catalytic activity and the asymmetric induction influenced by the structure of organocatalysts and the reaction condition are also discussed.
引用
收藏
页码:76 / 86
页数:11
相关论文
共 43 条
[31]   Catalytic reactions in ionic liquids [J].
Sheldon, R .
CHEMICAL COMMUNICATIONS, 2001, (23) :2399-2407
[32]   Organocatalytic asymmetric epoxidation of olefins by chiral ketones [J].
Shi, Y .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :488-496
[33]   Schiff base catalysts for the asymmetric Strecker reaction identified and optimized from parallel synthetic libraries [J].
Sigman, MS ;
Jacobsen, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (19) :4901-4902
[34]   Asymmetric Mannich reactions with in situ generation of carbamate-protected imines by an organic catalyst [J].
Song, Jun ;
Shih, Hui-Wen ;
Deng, Li .
ORGANIC LETTERS, 2007, 9 (04) :603-606
[35]   The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids:: Enantioselective synthesis of β-amino acids [J].
Song, Jun ;
Wang, Yi ;
Deng, Li .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (18) :6048-6049
[36]   Asymmetric catalysis by chiral hydrogen-bond donors [J].
Taylor, MS ;
Jacobsen, EN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (10) :1520-1543
[37]   Direct enantio- and diastereoselective Mannich reactions of malonate and β-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivative [J].
Tillman, AL ;
Ye, JX ;
Dixon, DJ .
CHEMICAL COMMUNICATIONS, 2006, (11) :1191-1193
[38]   Highly diastereloselective asymmetric Mannich reactions of 1,3-dicarbonyls with acyl imines [J].
Ting, A ;
Lou, S ;
Schaus, SE .
ORGANIC LETTERS, 2006, 8 (10) :2003-2006
[39]   Chiral Bronsted acid-catalyzed direct Mannich reactions via electrophilic activation [J].
Uraguchi, D ;
Terada, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (17) :5356-5357
[40]  
Wang K. C., 2003, Chinese Pharmaceutical Journal (Taipei), V55, P87