Stereospecific Friedel-Crafts Alkylation of Aromatic Compounds: Synthesis of Optically Active 2- and 3-Arylalkanoic Esters

Article abstract of DOI:10.1021/jo00001a037

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 (40-84percent) and in good to excellent optical yields (61-97percent).As usually occurs in Friedel-Crafts alkylation reactions, poor regioselectivity was observed.