OPTICALLY-ACTIVE SULFOXIDES BY ENANTIOSPECIFIC REACTIONS OF BROMOVINYL ARYL SULFOXIDES WITH GRIGNARD-REAGENTS

被引:36
作者
CARDELLICCHIO, C [1 ]
FIANDANESE, V [1 ]
NASO, F [1 ]
SCILIMATI, A [1 ]
机构
[1] UNIV BARI,DIPARTIMENTO CHIM,CNR,CTR STUDIO METODOL INNOVAT SINTESI ORGAN,VIA AMENDOLA 173,I-70126 BARI,ITALY
关键词
SULFOXIDE; ORGANOMAGNESIUM; HALOALKENES; ENANTIOSPECIFICITY; OXIDATION;
D O I
10.1016/S0040-4039(00)61207-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Optically active bromovinyl aryl sulfoxides were subjected to reactions with phenyl- or alkyl-magnesium compounds, with the production of optically active diaryl or aryl alkyl sulfoxides, with inversion of configuration. The enantiospecificity of the process was found to be 98-100%.
引用
收藏
页码:5121 / 5124
页数:4
相关论文
共 27 条
[1]  
Andersen K. K., 1988, CHEM SULPHONES SULPH, p[823, 55]
[2]   ASYMMETRIC OXIDATION OF 1,3-DITHIOLANES - A ROUTE TO THE OPTICAL RESOLUTION OF CARBONYL-COMPOUNDS [J].
BORTOLINI, O ;
DIFURIA, F ;
LICINI, G ;
MODENA, G ;
ROSSI, M .
TETRAHEDRON LETTERS, 1986, 27 (51) :6257-6260
[3]   REACTIONS OF 2-HALOVINYL ARYL SULFOXIDES WITH ORGANOMETALLIC REAGENTS [J].
CARDELLICCHIO, C ;
FIANDANESE, V ;
NASO, F .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1718-1722
[4]  
CARDELLICCHIO C, 1985, THESIS U BARI
[5]  
CARDELLICCHIO C, 1991, GAZZ CHIM ITAL, P11
[6]   ENANTIOSELECTIVE OXIDATION OF BETA-HYDROXYTHIOETHERS .1. SYNTHESIS OF OPTICALLY-ACTIVE ALCOHOLS AND EPOXIDES [J].
CONTE, V ;
DIFURIA, F ;
LICINI, G ;
MODENA, G ;
SBAMPATO, G ;
VALLE, G .
TETRAHEDRON-ASYMMETRY, 1991, 2 (04) :257-276
[7]   A CONVENIENT FAMILY OF CHIRAL SHIFT-REAGENTS FOR MEASUREMENT OF ENANTIOMERIC EXCESSES OF SULFOXIDES [J].
DESHMUKH, M ;
DUNACH, E ;
JUGE, S ;
KAGAN, HB .
TETRAHEDRON LETTERS, 1984, 25 (32) :3467-3470
[8]  
DIFURIA F, 1984, SYNTHESIS-STUTTGART, P325
[9]  
DRABOWICZ J, 1989, CROAT CHEM ACTA, V62, P423
[10]  
DRABOWICZ J, 1988, CHEM SULPHONES SULPH, P233