Stereoselective and stereospecific synthesis of 2-alkylidene-3-methylene succinic acid dimethyl esters

被引：13

作者：

Béji, F

Lebreton, J

Villiéras, J

Amri, H

机构：

[1] Fac Sci, Lab Chim Organ & Organomet, Tunis 1060, Tunisia

[2] Fac Sci & Tech, UMR CNRS 6513, Lab Synth Organ, F-44322 Nantes 3, France

来源：

SYNTHETIC COMMUNICATIONS | 2002年 / 32卷 / 21期

关键词：

D O I：

10.1081/SCC-120014031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Alkyl-2,3-dimethoxycarbonyl-1,3-butadienes 4 were synthesized via two different routes. In the first route, the Wittig-Horner reaction of the readily available phosphonate 2 with various aldehydes yielded the corresponding 1,3-dienes 4 with a good E stereoselectivity. The second route, using alpha-(bromomethyl) fumarate 1 under basic conditions, provides stereospecifically pure (E)-1,3-dienes 4.

引用

收藏

页码：3273 / 3278

页数：6

相关论文

共 26 条

[1] PYROLYSIS OF ESTERS .24. 2,3-DICARBOXY-1,3-BUTADIENE [J].

BAILEY, WJ ;

YATES, ET ;

HUDSON, RL .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (03) :828-&

[2]

Ballini R, 1999, SYNTHESIS-STUTTGART, P1236

[3] A DIRECT METHOD FOR THE SYNTHESIS OF POLYFUNCTIONALIZED UNSATURATED CARBONYL DERIVATIVES BY MICHAEL ADDITION OF NITROALKANES TO ENEDIONES WITH THE HELP OF DBU [J].

BALLINI, R ;

BOSICA, G .

TETRAHEDRON, 1995, 51 (14) :4213-4222

[4] Synthesis of α-alkylidene-β-ethoxycarbonyl cyclopentanones and -γ-butyrolactones [J].

Beji, F ;

Besbes, R ;

Amri, H .

SYNTHETIC COMMUNICATIONS, 2000, 30 (21) :3947-3954

[5] TEAF mediated hydroxylation of allylic bromide: A facile synthesis of 4-methoxycarbonyl-2(5H)-furanone [J].

Beltaief, I ;

Besbes, R ;

Amri, H ;

Villieras, J .

TETRAHEDRON LETTERS, 1997, 38 (05) :813-814

[6] (Z)-dimethyl α-(bromomethyl)fumarate, an efficient intermediate for the selective synthesis of dimethyl 3-alkyl itaconates and 2-alkyl 3-carbomethoxy-γ-lactams [J].

Beltaïef, I ;

Besbes, R ;

Ben Amor, F ;

Amri, H ;

Villiéras, M ;

Villiéras, J .

TETRAHEDRON, 1999, 55 (13) :3949-3958

[7]

Besbes R, 1997, INDIAN J CHEM B, V36, P5

[8] THE MICHAELIS-ARBUZOV REARRANGEMENT [J].

BHATTACHARYA, AK ;

THYAGARAJAN, G .

CHEMICAL REVIEWS, 1981, 81 (04) :415-430

[9] UNSATURATED LACTONES - SOME ESTERS OF ACONIC AND COUMALIC ACIDS [J].

CAMPBELL, NR ;

HUNT, JH .

JOURNAL OF THE CHEMICAL SOCIETY, 1947, (SEP) :1176-1179

[10]

Chamakh A, 2000, SYNTHESIS-STUTTGART, P295