CYCLIZATION OF GAMMA,DELTA-EPOXY-ALPHA-CYANOSULPHONES - A SIMPLE, DIASTEREOSELECTIVE ROUTE TO CYCLOPROPANE CARBOXYLIC-ACIDS

被引:23
作者
BENEDETTI, F
BERTI, F
RISALITI, A
机构
[1] Dipartimento di Scienze Chimiche, Università di Trieste, I-34127 Trieste
关键词
D O I
10.1016/0040-4039(93)85066-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
cyclisation of alpha-cyano-alpha-sulphonyl-gamma,delta-epoxy carbanions proceeds with high yields and complete diastereoselectivity, to yield cyclopropanolactones, useful intermediates in the synthesis of cis-substituted cyclopropane carboxylic acids.
引用
收藏
页码:6443 / 6446
页数:4
相关论文
共 13 条
[1]  
ACHINI R, 1975, TETRAHEDRON LETT, P369
[2]   REGIOSELECTIVITY IN CYCLIZATION OF BETA,GAMMA-EPOXY CARBANIONS - APPLICATION TO TOTAL SYNTHESIS OF TRANS-CHRYSANTHEMIC ACID [J].
BABLER, JH ;
TORTORELLO, AJ .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (05) :885-887
[3]   METHYL EFFECTS IN THE CYCLIZATION OF GAMMA-EPOXY BIS-SULFONES [J].
BENEDETTI, F ;
BERTI, F ;
FABRISSIN, S ;
GIANFERRARA, T ;
RISALITI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) :3530-3537
[4]  
BENEDETTI F, IN PRESS J ORG CHEM
[5]   MAGNESIUM IN METHANOL - SUBSTITUTE FOR SODIUM AMALGAM IN DESULFONYLATION REACTIONS [J].
BROWN, AC ;
CARPINO, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) :1749-1750
[6]   PYRETHRINS AND RELATED COMPOUNDS .19. GEOMETRICAL AND OPTICAL ISOMERS OF 2,2-DIMETHYL-3-(2,2-DICHLOROVINYL)-CYCLOPROPANECARBOXYLIC ACID AND INSECTICIDAL ESTERS WITH 5-BENZYL-3-FURYLMETHYL AND 3-PHENOXYBENZYL ALCOHOLS [J].
BURT, PE ;
ELLIOTT, M ;
FARNHAM, AW ;
JANES, NF ;
NEEDHAM, PH ;
PULMAN, DA .
PESTICIDE SCIENCE, 1974, 5 (06) :791-799
[7]  
FICINI J, 1976, TETRAHEDRON LETT, P2441
[8]   STEREOCHEMISTRY OF ADDITION OF ORGANOCOPPER REAGENTS AND OF THE HYDRIDE ION TO 1-(ARYLSULFONYL)BICYCLO[1.1.0]BUTANES [J].
GAONI, Y ;
TOMAZIC, A ;
POTGIETER, E .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16) :2943-2947
[10]  
KASATKIN AN, 1990, TETRAHEDRON LETT, P4915