HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE PREPARATION OF Z-SILYL ENOL ETHERS AND Z-ENOL ESTERS FROM KETONES VIA MANGANESE ENOLATES

被引:19
作者
CAHIEZ, G
FIGADERE, B
CLERY, P
机构
[1] Laboratoire de Chimie des Organoéléments, associé au CNRS Université P. et M. Curie, F-75252 Paris Cédex 05
关键词
D O I
10.1016/S0040-4039(00)73415-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mn-enolates are easily and quantitatively obtained under mild conditions (THF, -10 degrees C to rt, 1h) by treatment of ketones with aromatic Mn-amides such as Ph(Me)NMnZ. They allow to prepare Z silyl enol ethers and Z enol esters in high yields and with an excellent regio- and stereoselectivity (kinetic product: greater than or equal to 99%, Z/E: 93/7 to 100/0).
引用
收藏
页码:6295 / 6298
页数:4
相关论文
共 12 条
[1]  
BROWNBRIDGE P, 1983, SYNTHESIS-STUTTGART, P85
[2]  
BROWNBRIDGE P, 1983, SYNTHESIS-STUTTGART, P1
[3]   HIGHLY REGIOSELECTIVE MONOALKYLATION OF KETONES VIA MANGANESE ENOLATES PREPARED FROM MANGANESE AMIDES [J].
CAHIEZ, G ;
FIGADERE, B ;
CLERY, P .
TETRAHEDRON LETTERS, 1994, 35 (19) :3065-3068
[4]   HIGHLY REGIOSELECTIVE MONOALKYLATION OF KETONES VIA MANGANESE ENOLATES PREPARED FROM LITHIUM ENOLATES [J].
CAHIEZ, G ;
CHAU, K ;
CLERY, P .
TETRAHEDRON LETTERS, 1994, 35 (19) :3069-3072
[5]  
CAHIEZ G, 1991, Patent No. 11814
[6]  
CAHIEZ G, 1990, Patent No. 373993
[7]  
CAHIEZ G, 1993, Patent No. 6071
[8]  
CAHIEZ G, 1990, Patent No. 16413
[9]  
CAHIEZ G, 1988, Patent No. 8815806
[10]  
HEATHCOCK CH, 1984, ASYMMETRIC SYNTHESIS, V3, P111