Enantioselective synthesis of both enantiomers of 3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone

Article abstract of DOI:10.1016/S0040-4039(99)01383-0

The chiral auxiliaries (R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone were obtained in good yield and e.e. by enantioselective reduction of 4,4-dimethyl-1-phenylpyrrolidine-2,3-dione with (-)- and (+)-B-chlorodiisopinocamphenylborane, (-)- and (+)-DIP-Chloride, respectively. The (R)-enantiomer was also obtained by enantioselective hydrogenation of the same precursor using a complex of 1,5-cyclooctadiene Rh(I) and (2S,4S)-1-(tert-butoxycarbonyl)-4-(diphenylphosphino)-2-(diphenylphosphinomethyl )pyrrolidine, (S,S)-BPPM, as the chiral catalyst.