A stereodivergent approach to amino acids, amino alcohols, or oxazolidinones of high enantiomeric purity.

(-)-Menthone, an inexpensive chiral auxiliary, was used to prepare both enantiomers of alpha-amino acids, amino alcohols, or oxazolidinones. The sequence includes the S(N)2' displacement by a cuprate reagent and a Curtius rearrangement as key steps.