A study of 4-substituted 5,5-diaryl oxazolidin-2-ones as efficacious chiral auxiliaries

Article abstract of DOI:10.1016/S0040-4039(98)01412-9

A series of three 5,5-diaryl substituted oxazolidin-2-ones (diphenyl, dinaphthyl and ditolyl) have been prepared and shown to be particularly effective chiral auxiliaries to afford high yields and diastereoselectivities for alkylation and azidations of their N-acyl derivatives. The 5,5-ditolyl oxazolidin-2-one proved to be particularly efficacious in terms of diastereoselectivity, yield and solubility.