STEREOSPECIFIC FRIEDEL-CRAFTS ALKYLATION OF AROMATIC-COMPOUNDS - SYNTHESIS OF OPTICALLY-ACTIVE 2-ARYLALKANOIC AND 3-ARYLALKANOIC ESTERS

The alkylation of aromatic compounds, such as benzene, toluene, chlorobenzene, and naphthalene, with optically active (S)-alkyl 2-(sulfonyloxy)propionates and (R)-alkyl 3-(sulfonyloxy)butanoates in the presence of AlCl3 afforded optically active (S)-alkyl 2-arylpropionates and (S)-alkyl 3-arylbutanoates in fair to good chemical yields (40-84\%) and in good to excellent optical yields (61-97\%). As usually occurs in Friedel-Crafts alkylation reactions, poor regioselectivity was observed.