Enantio- and diastereoselective, stereospecific Mannich-type reactions in water

被引:145
作者
Hamada, T [1 ]
Manabe, K [1 ]
Kodayashi, S [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
D O I
10.1021/ja048607t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalytic asymmetric Mannich-type reactions in water proceeded in high yields and selectivities using a combination of ZnF2 and a chiral diamine that has the methoxy groups on the aromatic rings. In these reactions, either syn- or anti-Mannich adducts were stereospecifically obtained from (E)- or (Z)-silicon enolate, in contrast with most asymmetric Mannich-type reactions. Copyright © 2004 American Chemical Society.
引用
收藏
页码:7768 / 7769
页数:2
相关论文
共 30 条
[1]  
[Anonymous], 1994, SURFACTANT ENHANCED
[2]  
Cramer C. J., 1994, STRUCTURE REACTIVITY
[3]  
Fendler J. H., 1975, CATALYSIS MICELLAR M, P386
[4]   Enantioselective radical addition to N-acyl hydrazones mediated by chiral Lewis acids [J].
Friestad, GK ;
Shen, YH ;
Ruggles, EL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (41) :5061-5063
[5]  
Grieco P.A., 1998, Organic synthesis in water
[6]   Catalytic asymmetric allylation of hydrazono esters in aqueous media by using ZnF2-chiral diamine [J].
Hamada, T ;
Manabe, K ;
Kobayashi, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (33) :3927-3930
[7]  
Holland PM, 1992, ACS Symposium Series
[8]   Efficient and practical Ag-catalyzed cycloadditions between arylimines and the Danishefsky diene [J].
Josephsohn, NS ;
Snapper, ML ;
Hoveyda, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (14) :4018-4019
[9]   Asymmetric hydrocyanation of hydrazones catalyzed by lanthanide-PYBOX complexes [J].
Keith, JM ;
Jacobsen, EN .
ORGANIC LETTERS, 2004, 6 (02) :153-155
[10]   Catalytic asymmetric aldol reactions in water using a chiral Lewis-acid-surfactant-combined catalyst [J].
Kobayashi, S ;
Mori, Y ;
Nagayama, S ;
Manabe, K .
GREEN CHEMISTRY, 1999, 1 (04) :175-177