ASYMMETRIC PROTONATION OF ENOLATES

被引:50
作者
POTIN, D
WILLIAMS, K
REBEK, J
机构
[1] UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260
[2] MIT,DEPT CHEM,CAMBRIDGE,MA 02139
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1990年 / 29卷 / 12期
关键词
D O I
10.1002/anie.199014201
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Efficient chiral proton sources have long been the organic chemist's dream. With the lactam 1 based on Kemp's tricarboxylic acid, cyclic enolates have now been protonated with an enantiomeric excess (ee) of up to 91%. The reason for the high ee values is the asymmetric microenvironment of the acidic NH group.
引用
收藏
页码:1420 / 1422
页数:3
相关论文
共 18 条
[1]   NEW CHIRAL AUXILIARIES FOR THERMAL CYCLOADDITIONS [J].
CURRAN, DP ;
JEONG, KS ;
HEFFNER, TA ;
REBEK, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9238-9240
[2]   LIGAND-EXCHANGE IN ASYMMETRIC REACTIONS OF LITHIUM ENOLATES - APPLICATION TO THE DERACEMIZATION OF ALPHA-AMINO-ACIDS [J].
DUHAMEL, L ;
FOUQUAY, S ;
PLAQUEVENT, JC .
TETRAHEDRON LETTERS, 1986, 27 (41) :4975-4978
[3]   DERACEMIZATION BY ENANTIOSELECTIVE PROTONATION .4. AN IMPROVED METHOD FOR THE ENANTIOMERIC ENRICHMENT OF ALPHA-AMINOACIDS USING METALATION BY MEANS OF CHIRAL AMIDES [J].
DUHAMEL, L ;
PLAQUEVENT, JC .
TETRAHEDRON LETTERS, 1980, 21 (26) :2521-2524
[4]  
DUHAMEL L, 1984, B SOC CHIM FR, V2, P421
[5]  
FARINES M, 1970, B SOC CHIM FR, P332
[7]  
Gerlach, 1987, ANGEW CHEM, V99, P1323
[8]   ENANTIOSELECTIVE PROTONATION OF CARBANIONS WITH CHIRAL PROTON SOURCES [J].
GERLACH, U ;
HUNIG, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (12) :1283-1285
[9]   NEW CHIRAL AUXILIARIES FOR ENOLATE ALKYLATIONS [J].
JEONG, KS ;
PARRIS, K ;
BALLESTER, P ;
REBEK, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (05) :555-556
[10]  
JEONG KS, 1990, ANGEW CHEM, V102, P550