Synthesis of chiral 2-oxazolidinones, 2-oxazolines, and their analogs

Chiral five-membered ring 2-oxazolidinones and six-membered ring 1,3-oxazinan-2-ones are synthesized from the corresponding amino alcohols with complete inversion or retention of stereochemistry. Chiral 5-substituted 2-oxazolines and 6-substituted 2-oxazines are also synthesized from the same starting materials with inversion of stereochemistry through an intramolecular SN2 reaction. These compounds are useful intermediates in organic synthesis and crucial building blocks for many pharmaceutical compounds.