ENANTIOSELECTIVE OXIDATION OF THIOETHERS1 - AN EASY ROUTE TO ENANTIOPURE C-2 SYMMETRICAL BIS-METHYLSULFINYLBENZENES

被引:25
作者
BENDAZZOLI, P [1 ]
DIFURIA, F [1 ]
LICINI, G [1 ]
MODENA, G [1 ]
机构
[1] UNIV MARZOLO 1,DIPARTIMENTO CHIM ORGAN,CTR MECCAN REAZ ORGAN,CNR,I-35131 PADUA,ITALY
关键词
ENANTIOSELECTIVE OXIDATION; THIOETHERS; BIS-METHYLTHIOBENZENES; BIS-METHYLSULFINYLBENZENES;
D O I
10.1016/S0040-4039(00)60497-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The direct oxidation of bis-methylthioethers 1 by t-butyl hydroperoxide, titanium tetra-iso-propilate, and (+)-diethyltartrate, affords the almost enantiomerically pure dl bis-methylsulfinylbenzenes 2 (e.e. greater-than-or-equal-to 99%) in a process which is also characterized by a very high diastereoselectivity.
引用
收藏
页码:2975 / 2978
页数:4
相关论文
共 8 条
[1]   CHIRAL, BISFUNCTIONALIZATION OF SUBSTRATES - A POWERFUL STRATEGY FOR THE ASYMMETRIC-SYNTHESIS OF C2 SYMMETRIAL COMPOUNDS AND ITS APPLICATION TO THE SYNTHESIS OF ENANTIOMERICALLY PURE TRANS-1,3-DITHIANE 1,3-DIOXIDE [J].
AGGARWAL, VK ;
EVANS, G ;
MOYA, E ;
DOWDEN, J .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6390-6391
[2]  
DAVIES GS, 1992, TETRAHEDRON LETT, V33, P1117
[3]   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
[4]  
DIFURIA F, 1984, SYNTHESIS-STUTTGART, P325
[5]  
FURLANI M, 1992, IN PRESS PHOSPHORUS
[6]  
OSSU S, 1992, TETRAHEDRON LETT, V33, P2053
[7]  
Patai S., 1988, CHEM SULPHONES SULPH