(R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone, New Chiral Auxiliaries for the Asymmetric Synthesis of α-Arylpropanoic Acids.

Article abstract of DOI:10.1016/0957-4166(95)00110-B

Reaction of rac-α-arylpropanoyl chlorides with (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone (R)- and (S)-1, in the presence of triethylamine, under standard esterification conditions, gave (R,R)- and (S,S)-3, respectively, with high diastereoselectivity.Controlled acidic hydrolysis afforded the corresponding (R)- or (S)-α-arylpropanoic acids with high enantioselectivity, the chiral auxiliary being recovered efficiently.