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

The chiral auxiliaries (R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl-2-pyrro lidi none were obtained in good yield and e.e. by enantioselective reductio n of 4,4-dimethyl-1-phenylpyrrolidine-2,3-dione with (-)- and (+)-B-chlorod iisopinocamphenylborane, (-)- and (+)-DIP-Chloride(R), respectively. The (R )-enantiomer was also obtained by enantioselective hydrogenation of the sam e precursor using a complex of 1,5-cyclooctadiene Rh(I) and (2S,4S)-1-(tert -butoxycarbonyl)-4-(diphenylphosphino)-2-(diphenylphosphinomethyl)pyrrolidi ne,(S,S)-BPPM, as the chiral catalyst. (C) 1999 Elsevier Science Ltd. All r ights reserved.