ENANTIOSELECTIVE FLUORINATION OF ORGANIC-MOLECULES .1. SYNTHETIC STUDIES OF THE AGENTS FOR ELECTROPHILIC, ENANTIOSELECTIVE FLUORINATION OF CARBANIONS

In order to develop novel methods for electrophilic and enantioselecti ve fluorination of active methine compounds, preliminary experiments w ere carried out, The N-tosyl derivative 5 obtained from D-phenylglycin e was fluorinated with FCIO3 or diluted F-2 gas to give the N-fluoro-N -tosyl derivative 6. N-Tosyl- or N-mesyl-(S)-alpha-phenethylamine 7 or 8 was subjected to FCIO3 fluorination to produce the corresponding N- fluoro derivative, 10 or 11, respectively, Enantioselective fluorinati on of some methine compounds was attempted employing the above N-fluor o agents. Best result was obtained when 2-benzyl-1-tetralone/KHMDS was treated with 10 to produce the fluorinated tetralone 17 in 53% yield with enantiomeric excess (ee) of 48%.