ETHYLMAGNESIUM BROMIDE MEDIATED DESULFINYLATION OF ALPHA-HALO-BETA-KETOSULFOXIDES GIVING ALPHA-HALOKETONES, AND TRAPPING OF THE MAGNESIUM ENOLATE INTERMEDIATE

被引:12
作者
SATOH, T [1 ]
ONDA, K [1 ]
ITOH, N [1 ]
YAMAKAWA, K [1 ]
机构
[1] SCI UNIV TOKYO,FAC PHARMACEUT SCI,ICHIGAYA FUNAGAWARA MACHI,SHINJUKU KU,TOKYO 162,JAPAN
关键词
D O I
10.1016/0040-4039(91)80094-M
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of alpha-halo-beta-ketosulfoxides with EtMgBr gives alpha-haloketones in high yields after protonation of the magnesium enolates. Trapping of the magnesium enolates with various electrophiles is also carried out.
引用
收藏
页码:5599 / 5600
页数:2
相关论文
共 19 条
[1]  
Block E., 1978, REACTIONS ORGANOSULF
[2]   REACTIONS OF PYRIDYL AND QUINOLYL SULFOXIDES WITH GRIGNARD-REAGENT - A CONVENIENT PREPARATION OF PYRIDYL AND QUINOLYL GRIGNARD-REAGENTS [J].
FURUKAWA, N ;
SHIBUTANI, T ;
MATSUMURA, K ;
FUJIHARA, H ;
OAE, S .
TETRAHEDRON LETTERS, 1986, 27 (33) :3899-3902
[3]   A NEW SOURCE FOR GENERATION OF BENZYNE AND PYRIDYNE - REACTIONS OF ORTHO-HALOPHENYL (OR 3-BROMO-4-PYRIDYL) PHENYL SULFOXIDES WITH GRIGNARD-REAGENTS [J].
FURUKAWA, N ;
SHIBUTANI, T ;
FUJIHARA, H .
TETRAHEDRON LETTERS, 1987, 28 (24) :2727-2730
[4]  
Iriuchisima S., 1970, SYNTHESIS-STUTTGART, P588
[5]  
Patai S., 1988, CHEM SULPHONES SULPH
[6]   ALPHA-FLUOROCARBONYL COMPOUNDS AND RELATED CHEMISTRY [J].
ROZEN, S ;
FILLER, R .
TETRAHEDRON, 1985, 41 (07) :1111-1153
[7]   ALPHA,BETA-EPOXY SULFOXIDES AS USEFUL INTERMEDIATE IN ORGANIC-SYNTHESIS .14. THE PRACTICAL PROCEDURE FOR A PREPARATION OF 1-CHLOROALKYL PARA-TOLYL SULFOXIDES IN HIGH OPTICALLY-ACTIVE FORM - A VERY SHORT SYNTHESIS OF OPTICALLY-ACTIVE DISPARLURE [J].
SATOH, T ;
OOHARA, T ;
UEDA, Y ;
YAMAKAWA, K .
TETRAHEDRON LETTERS, 1988, 29 (03) :313-316
[8]   GENERATION OF ENOLATES FROM ALPHA,BETA-EPOXY SULFOXIDES WITH LITHIUM DIMETHYLCUPRATE - A NOVEL SYNTHESIS OF ALDOLS AND SOME TRIAL TO TRAP THE ENOLATES [J].
SATOH, T ;
SUGIMOTO, A ;
ITOH, M ;
YAMAKAWA, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (09) :2942-2947
[9]   ALPHA-BETA-EPOXY SULFOXIDES AS USEFUL INTERMEDIATES IN ORGANIC-SYNTHESIS .8. STEREOSPECIFIC DESULFINYLATION OF ALPHA-BETA-EPOXY SULFOXIDES WITH BUTYLLITHIUM - A NEW SYNTHESIS OF EPOXIDES AND ALLYLIC ALCOHOLS FROM CARBONYL-COMPOUNDS [J].
SATOH, T ;
KANEKO, Y ;
YAMAKAWA, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (08) :2463-2470
[10]   A NOVEL-APPROACH TO THE SYNTHESIS OF CHIRAL EPOXIDES AND ALLYLIC ALCOHOLS BY THE USE OF OPTICALLY-ACTIVE PARA-TOLYL SULFINYL GROUP AS A CHIRAL AUXILIARY [J].
SATOH, T ;
OOHARA, T ;
YAMAKAWA, K .
TETRAHEDRON LETTERS, 1988, 29 (23) :2851-2854