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

Abstract

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 S N2 reaction. These compounds are useful intermediates in organic synthesis and crucial building blocks for many pharmaceutical compounds.