PALLADIUM-CATALYZED ALKYLATIVE CYCLIZATION OF 2,3-BUTADIANYLMALONATES TO GAMMA-LACTONES

被引:32
作者
BESSON, L [1 ]
BAZIN, J [1 ]
GORE, J [1 ]
CAZES, B [1 ]
机构
[1] UNIV LYON 1,ESCIL,CNRS,CHIM ORGAN LAB 1,F-69622 VILLEURBANNE,FRANCE
关键词
D O I
10.1016/S0040-4039(00)76649-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalysed reaction of vinyl halides with the anions of 1,1-dimethyl-2,3-butadienylmalonates leads to 4-dienyl gamma-lactones through an unexpected alkylative O-cyclisation pathway due to the steric demand of the alpha-allenic gem-dimethyl group.
引用
收藏
页码:2881 / 2884
页数:4
相关论文
共 21 条
[1]   SYNTHESIS OF 1,3-DIENES AND FUNCTIONALIZED STYRENES BY CATALYTIC CARBOPALLADATION OF ALLENES [J].
AHMAR, M ;
CAZES, B ;
GORE, J .
TETRAHEDRON LETTERS, 1984, 25 (40) :4505-4508
[2]  
AHMAR M, 1985, TETRAHEDRON LETT, V6, P3795
[3]  
AHMAR M, 1987, TETRAHEDRON, V435, P513
[4]   SYNTHETIC METHODOLOGY INVOLVING THE CARBOPALLADATION OF ALLENES [J].
CAZES, B .
PURE AND APPLIED CHEMISTRY, 1990, 62 (10) :1867-1878
[5]   SYNTHESIS OF (+) DICTYOPTERENE A CONSTITUENT OF MARINE BROWN-ALGAE AND (+) DICTYOPTERENE C' BY CHIRALITY TRANSFER OF OPTICALLY-ACTIVE ALLYLIC BENZOATE WITH PALLADIUM (O) CATALYST [J].
COLOBERT, F ;
GENET, JP .
TETRAHEDRON LETTERS, 1985, 26 (23) :2779-2782
[6]   ORGANOPALLADIUM COMPOUNDS FROM ALPHA-ALLENIC ALCOHOL ESTERS - REACTIONS WITH DELOCALIZED ANIONS [J].
DJAHANBINI, D ;
CAZES, B ;
GORE, J .
TETRAHEDRON, 1987, 43 (15) :3441-3452
[7]  
DJAHANBINI D, 1984, TETRAHEDRON LETT, V25, P845
[8]  
FRIESS B, 1992, B SOC CHIM FR, V129, P273
[9]   VINYL TRIFLUOROSULFONATES IN THE CARBOPALLADATION OF ALLENIC HYDROCARBONS [J].
FRIESS, B ;
CAZES, B ;
GORE, J .
TETRAHEDRON LETTERS, 1988, 29 (33) :4089-4092
[10]   PALLADIUM-CATALYZED PREPARATION OF CARBON AND OXYGEN SPIROCYCLES [J].
GODLESKI, SA ;
VALPEY, RS .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (02) :381-383