MILD ALPHA-FLUORINATION OF ENANTIOMERICALLY PURE BETA-KETOSULFOXIDES BY F-TEDA-BF4

Authors
ARNONE A BRAVO P FRIGERIO M SALANI G VIANI F ZANDA M ZAPPALA C
Citation
A. Arnone et al., MILD ALPHA-FLUORINATION OF ENANTIOMERICALLY PURE BETA-KETOSULFOXIDES BY F-TEDA-BF4, Journal of fluorine chemistry, 84(1), 1997, pp. 79-82
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear
Journal title
Journal of fluorine chemistry → ACNP
ISSN journal
00221139
Volume
84
Issue
1
Year of publication
1997
Pages
79 - 82
Database
ISI
SICI code
0022-1139(1997)84:1<79:MAOEPB>2.0.ZU;2-5
Abstract
A wide range of cu-sodium derivatives of chiral and enantiomerically p ure beta-ketosulfoxides have been regioselectively fluorinated with th e 'F+' fluorinating agent F-TEDA-BF4 without affecting the sulfinyl st ereogenic center. alpha-Monofluoro-beta-ketosulfoxides produced in thi s reaction can undergo further fluorination providing the correspondin g alpha,alpha-difluoro derivatives, easily transformed by deacylation into enantiomerically pure (S)-difluoromethyl-p-tolylsulfoxide. (C) 19 97 Elsevier Science S.A.