Asymmetric aldol and alkylation reactions mediated by the 'quat' chiral auxiliary (R)-(-)-5-methyl-3,3-dimethyl-2-pyrrolidinone

Article abstract of DOI:10.1016/0040-4039(94)85223-5

Enolates derived from the N-propionoyl derivative of the 'quat' chiral auxiliary (R)-(-)-5-methyl-3,3-dimethyl-2-pyrrolidinone undergo highly stereoselective aldol and alkylation reactions. Removal of the auxiliary has been demonstrated with LiOH, PhCH₂OLi, MeOMgBr and LiAlH₄ to generate respectively (2R,3R)-3-hydroxy-2-methyl-3-phenylpropionic acid in homochiral form, and with 96% e.e. (S)-2-methyl-3-phenylpropionic acid and derived methyl and benzyl esters and with >94% e.e. (S)-2-methyl-3-phenylpropanol.