Mild alpha-fluorination of enantiomerically pure beta-ketosulfoxides by F-TEDA-BF4

被引：9

作者：

Arnone, A

Bravo, P

Frigerio, M

Salani, G

Viani, F

Zanda, M

Zappala, C

机构：

[1] POLITECN MILAN,DIPARTIMENTO CHIM,I-20131 MILAN,ITALY

[2] CNR,CTR STUDIO SOSTANZE ORGAN NAT,I-20131 MILAN,ITALY

来源：

JOURNAL OF FLUORINE CHEMISTRY | 1997年 / 84卷 / 01期

关键词：

fluorination; chiral sulfoxides; F-TEDA-BF4;

D O I：

10.1016/S0022-1139(97)00035-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A wide range of cu-sodium derivatives of chiral and enantiomerically pure beta-ketosulfoxides have been regioselectively fluorinated with the 'F+' fluorinating agent F-TEDA-BF4 without affecting the sulfinyl stereogenic center. alpha-Monofluoro-beta-ketosulfoxides produced in this reaction can undergo further fluorination providing the corresponding alpha,alpha-difluoro derivatives, easily transformed by deacylation into enantiomerically pure (S)-difluoromethyl-p-tolylsulfoxide. (C) 1997 Elsevier Science S.A.

引用

页码：79 / 82

页数：4

共 29 条

[1] SYNTHESIS OF FLUORINATED CHIRONS - STEREOSELECTIVE OXIRANE FORMATION BY REACTION OF DIAZOMETHANE ON 1-FLUORO-3-ARYLSULFINYL-2-PROPANONE AND RING-OPENING BY SELECTED NUCLEOPHILES [J].