Enediolates of carboxylic acids in synthesis:: Synthesis of γ-chloro-β-hydroxy acids

被引：0
作者：
Gil, S
Knecteman, M
Parra, M
Sotoca, E
机构：
[1] Univ Valencia, Dept Quim Organ, E-46100 Valencia, Spain
[2] Univ Nacl Litoral, Fac Ingn Quim, Dept Quim Organ, RA-3000 Santa Fe, Argentina
来源：
SYNTHESIS-STUTTGART | 2002年 / 02期
关键词：
neighbouring-group effects; diastereoselectivity; carboxylic acids; carbanions; lactones;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Enediolates from carboxylic acids react readily with cyclic alpha-chloroketones to give the corresponding gamma-chloro-beta-alkoxycarboxylate intermediates depending on the ring size. Small ring ketones lead to gamma-chloro-beta-hydroxy acids in a highly stereoselective way, whereas medium ring ketones give a mixture of beta,gamma-epoxy acids and gamma-lactones.
引用
收藏
页码：265 / 273
页数：9
相关论文
共 7 条
[1]   Lithium enediolates and dienediolates of carboxylic acids in synthesis: Alkylation with secondary halides [J].
Brun, EM ;
Gil, S ;
Mestres, R ;
Parra, M .
TETRAHEDRON, 1998, 54 (50) :15305-15320
[2]   Enediolates and dienediolates of carboxylic acids in synthesis.: Synthesis of β,γ-epoxyacids from α-chloroketones. [J].
Brun, EM ;
Gil, S ;
Mestres, R ;
Parra, M ;
Villar, F .
TETRAHEDRON LETTERS, 1998, 39 (09) :1055-1058
[3]  
Brun EM, 2000, SYNTHESIS-STUTTGART, P1160
[4]   SYNTHESIS OF DELTA1-BUTENOLIDES [J].
EPSTEIN, WW ;
SONNTAG, AC .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (11) :3390-&
[5]  
MEKELBURGER HB, 1991, FORMATION ENOLATES C, P99
[6]  
Thomson C.M., 1994, DIANION CHEM ORGANIC, P88
[7]   The cation complexation model predicts the experimental π-facial selectivity of 2-ax- and 2-eq-substituted cyclohexanones.: A detailed ab initio MO investigation [J].
Yadav, VK ;
Jeyaraj, DA ;
Balamurugan, R .
TETRAHEDRON, 2000, 56 (38) :7581-7589
1