Lewis base-catalyzed anti-selective Mannich-type reaction between trimethylsilyl enolates and aldimines

被引:24
作者
Takahashi, E
Fujisawa, H
Mukaiyama, T
机构
[1] Kitasato Inst, Ctr Basic Res, TCI, Kita Ku, Tokyo 1140003, Japan
[2] Kitasato Univ, Kitsato Inst Life Sci, Minato Ku, Tokyo 108864, Japan
关键词
D O I
10.1246/cl.2005.84
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Potassium or ammonium carboxylates catalyzed Mannich-type reaction between trimethylsilyl enolates and aldimines proceeded smoothly to afford the corresponding beta-amino carbonyl compounds in good to high yields with high anti selectivity.
引用
收藏
页码:84 / 85
页数:2
相关论文
共 20 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]   Lewis base-catalyzed Mannich-type reaction between aldimine and trimethylsilyl enolate [J].
Fujisawa, H ;
Takahashi, E ;
Nakagawa, T ;
Mukaiyama, T .
CHEMISTRY LETTERS, 2003, 32 (11) :1036-1037
[3]   A catalytic aldol reaction between ketene silyl acetals and aldehydes promoted by lithium amide under non-acidic conditions [J].
Fujisawa, H ;
Mukaiyama, T .
CHEMISTRY LETTERS, 2002, (02) :182-183
[4]   Lithium pyrrolidone catalyzed aldol reaction between aldehyde and trimethylsilyl enolate [J].
Fujisawa, H ;
Mukaiyama, T .
CHEMISTRY LETTERS, 2002, (08) :858-859
[5]   Enantio- and diastereoselective, stereospecific Mannich-type reactions in water [J].
Hamada, T ;
Manabe, K ;
Kodayashi, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (25) :7768-7769
[6]   Catalytic enantioselective addition to imines [J].
Kobayashi, S ;
Ishitani, H .
CHEMICAL REVIEWS, 1999, 99 (05) :1069-1094
[7]   Direct catalytic asymmetric Mannich-type reaction of hydroxyketone using a Et2Zn/Linked-BINOL complex:: Synthesis of either anti- or syn-β-amino alcohols [J].
Matsunaga, S ;
Yoshida, T ;
Morimoto, H ;
Kumagai, N ;
Shibasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) :8777-8785
[8]  
Miura K, 2000, ANGEW CHEM INT EDIT, V39, P1958, DOI 10.1002/1521-3773(20000602)39:11<1958::AID-ANIE1958>3.0.CO
[9]  
2-4
[10]   Lithium alkoxide-promoted Michael reaction between silyl enolates and α,β-unsaturated carbonyl compounds [J].
Mukaiyama, T ;
Tozawa, T ;
Fujisawa, H .
CHEMISTRY LETTERS, 2004, 33 (11) :1410-1411