Stereoselective electrochemical transformation of alkylidenecyanoacetates and malonate into (E)-3-substituted-2-cyanocyclopropane-1,1,2-tricarboxylates

被引:39
作者
Elinson, MN
Feducovich, SK
Starikova, ZA
Olessova, OS
Vereshchagin, AN
Nikishin, GI
机构
[1] ND Zelinskii Inst Organ Chem, Moscow 117913, Russia
[2] AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, Russia
基金
俄罗斯基础研究基金会;
关键词
electrochemical reactions; stereoselectivity; catalysis; cyclopropanes;
D O I
10.1016/S0040-4039(00)00733-4
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
Electrolysis of malonate and alkylidenecyanoacetates in alcohols in the presence of sodium bromide in an undivided cell results in the stereoselective formation of (E)-3-substituted 2-cyanocyclopropane-1,1,2-tricarboxylates in 75-85% yields. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4937 / 4941
页数:5
相关论文
共 12 条
[1]
BONAVENT G, 1964, B SOC CHIM FR, P2462
[2]
REACTIONS OF CARBANIONS WITH ELECTRON-ACCEPTORS [J].
BORDWELL, FG ;
CLEMENS, AH ;
SMITH, DE ;
BEGEMANN, J .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) :1151-1156
[3]
SYNTHESIS OF OPTICALLY-ACTIVE COMPOUNDS - A LARGE-SCALE PERSPECTIVE [J].
CROSBY, J .
TETRAHEDRON, 1991, 47 (27) :4789-4846
[4]
Electrochemical transformation of cyanoacetic ester and alkylidenecyanoacetic esters into 3-substituted 1,2-dicyanocyclopropane-1,2-dicarboxylates [J].
Elinson, MN ;
Feducovich, SK ;
Bushuev, SG ;
Pashchenko, DV ;
Nikishin, GI .
RUSSIAN CHEMICAL BULLETIN, 1998, 47 (06) :1133-1136
[5]
Elinson MN, 1998, MENDELEEV COMMUN, V8, P15
[6]
ELINSON MN, 1993, MENDELEEV COMMUN, P191
[7]
Jones G., 1967, ORGANICREACTIONS, V15, P204, DOI [DOI 10.1002/0471264180.OR015.02, 10.1002/0471264180.or015.02]
[8]
KRYSHTAL GV, 1980, IAN SSSR KH, P2420
[9]
CYCLOCONDENSATION REACTIONS FROM ELECTROGENERATED HALOMALONATE CARBANIONS COMPARED REACTIVITY OF BROMO AND CHLORO ANIONS AND INFLUENCE OF THE SUPPORTING-ELECTROLYTE CATION [J].
LEMENN, JC ;
SARRAZIN, J ;
TALLEC, A .
ELECTROCHIMICA ACTA, 1990, 35 (02) :563-566
[10]
SHELDRICK GM, 1994, SHELXTL VERSION 5 SO