AN EXPEDIENT STEREOSELECTIVE ACCESS TO (Z)-2-FLUOROALKENOATES

被引：21

作者：

CLEMENCEAU, D ^{[1
]}

COUSSEAU, J ^{[1
]}

机构：

[1] UNIV ANGERS,FAC SCI,CHIM ORGAN FONDAMENTALE & APPL LAB,2 BLD LAVOISIER,F-49045 ANGERS,FRANCE

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 43期

关键词：

2-FLUOROALKENOATES; (Z)-STEREOSELECTIVE SYNTHESIS;

D O I：

10.1016/S0040-4039(00)91826-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction between an aldehyde R-CHO and diethyl 2-oxo-3-fluorobutan-1,4-dioate as its sodium salt EtO2C-CO-CF-CO2Et-, Na+ mainly leads in THF to (Z)-2-fluoroalkenoates R-CH=CF-CO2Et (Z/E greater-than-or-equal-to 80/20), the Z-stereoselectivity depending on the bulk of the R group.

引用

页码：6903 / 6906

页数：4

共 22 条

[1] ETHYL PHENYLSULFINYL FLUOROACETATE, A NEW AND VERSATILE REAGENT FOR THE PREPARATION OF ALPHA-FLUORO-ALPHA,BETA-UNSATURATED CARBOXYLIC-ACID ESTERS [J].

ALLMENDINGER, T .

TETRAHEDRON, 1991, 47 (27) :4905-4914

[2]

BERGMANN ED, 1960, J CHEM SOC, P5261

[3] ORGANIC FLUORINE COMPOUNDS .40. FURTHER REACTIONS OF DIETHYL FLUORO-OXALOACETATE WITH ALDEHYDES [J].

BERGMANN, ED ;

SHAHAK, I ;

SALI, E ;

AIZENSHT.Z .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (10) :1232-&

[4] ORGANIC FLUORINE COMPOUNDS .25. FURTHER REACTION OF ALDEHYDES WITH DIETHYL FLUORO-OXALOACETATE [J].

BERGMANN, ED ;

SHAHAK, I .

JOURNAL OF THE CHEMICAL SOCIETY, 1961, (SEP) :4033-&

[5] STUDIES OF ORGANIC FLUORINE COMPOUNDS .4. SYNTHESIS OF ESTERS OF FLUORO-OXALOACETIC AND OF FLUOROPYRUVIC ACID [J].

BLANK, I ;

MAGER, J ;

BERGMANN, ED .

JOURNAL OF THE CHEMICAL SOCIETY, 1955, :2190-2193

[6] SYNTHESIS OF DIENIC FLUORINATED ANALOGS OF INSECT SEX-PHEROMONES [J].

CAMPS, F ;

COLL, J ;

FABRIAS, G ;

GUERRERO, A .

TETRAHEDRON, 1984, 40 (15) :2871-2878

[7]

GAULT H, 1963, B SOC CHIM FR, P711

[8]

GAULT H, 1960, CR HEBD ACAD SCI, V250, P1073

[9] ZINC(0)-COPPER(I) CHLORIDE PROMOTED REACTION OF METHYL DICHLOROFLUOROACETATE WITH CARBONYL-COMPOUNDS - A NEW EFFICIENT METHOD FOR THE SYNTHESIS OF METHYL (ZETA)-ALPHA-FLUORO-ALPHA,BETA-UNSATURATED CARBOXYLATES [J].

ISHIHARA, T ;

KUROBOSHI, M .

CHEMISTRY LETTERS, 1987, (06) :1145-1148

[10] ONE-POT SYNTHESIS OF ALPHA-FLUORO-ALPHA, BETA-UNSATURATED ESTERS FROM CHLOROMALONIC ESTER AND CARBONYL-COMPOUNDS USING SPRAY-DRIED POTASSIUM FLUORIDE [J].

KITAZUME, T ;

ISHIKAWA, N .

CHEMISTRY LETTERS, 1981, (09) :1259-1260

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