BETA-DIETHOXYPHOSPHORYLPROPIONIC ACID, A CONVENIENT REAGENT FOR THE SYNTHESIS OF BETA,GAMMA-UNSATURATED AMIDES

被引:8
作者
JANECKI, T [1 ]
BODALSKI, R [1 ]
机构
[1] TECH UNIV LODZ,INST ORGAN CHEM,PL-90924 LODZ,POLAND
关键词
D O I
10.1016/0040-4039(91)80796-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Beta-Diethoxyphosphorylpropionic acid (1) is converted into delta-substituted beta-(diethoxyphosphoryl)-delta-lactones 5 by LDA promoted reaction with carbonyl compounds 3. Aminolysis or alternatively a standard alkylation and aminolysis of 5 afford (E)-beta,delta-unsaturated amides 7 or 10 in good yield.
引用
收藏
页码:6231 / 6234
页数:4
相关论文
共 19 条
[1]  
AVOGARA P, 1977, ARTERY, P219
[2]  
CANONIA L, 1966, Patent No. 3231469
[3]  
HAEBERLE N, 1980, Patent No. 2830351
[4]  
JANECKI T, 1989, SYNTHESIS-STUTTGART, P506
[5]   NOTE ON A PREPARATION OF BETA,GAMMA-UNSATURATED CARBOXYLIC-ACID DERIVATIVES USING THE AMIDE ACETAL CLAISEN REARRANGEMENT [J].
JENKINS, PR ;
GUT, R ;
WETTER, H ;
ESCHENMOSER, A .
HELVETICA CHIMICA ACTA, 1979, 62 (06) :1922-1931
[6]  
KIRINO O, 1983, J PESTIC SCI, V8, P301
[7]   SYNTHESIS AND REACTIONS OF IODO LACTAMS [J].
KNAPP, S ;
LEVORSE, AT .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) :4006-4014
[8]   METALATED UNSATURATED AMIDES - REGIOSELECTIVE AND STEREOSELECTIVE GAMMA-ALKYLATION [J].
MAJEWSKI, M ;
MPANGO, GB ;
THOMAS, MT ;
WU, A ;
SNIECKUS, V .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (10) :2029-2045
[9]   THE WITTIG OLEFINATION REACTION AND MODIFICATIONS INVOLVING PHOSPHORYL-STABILIZED CARBANIONS - STEREOCHEMISTRY, MECHANISM, AND SELECTED SYNTHETIC ASPECTS [J].
MARYANOFF, BE ;
REITZ, AB .
CHEMICAL REVIEWS, 1989, 89 (04) :863-927
[10]  
MENTZER C, 1962, Patent No. 907841