Synthetic Versatility of 2-Oxazolone Heterocycle for Stereo-controlled Construction of 2-Amino Alcohols

Abstract

Synthetic potential of the simple heterocycle, 2-oxazolone, as a building block for 2-amino alcohols has been reviewed. Stereodefined introduction of easily replaceable groups to the olefinic moiety of the 2-oxazolone ring, followed by stereospecific and stepwise substitution, works well as a versatile strategy for the chiral synthesis of a wide variety of 2-amino alcohols of biological interest. Sterically constrained chiral 2-oxazolidinones and the derived 2-amino alcohols which are derived from cycloaddition of the 2-oxazolone to cyclic dienes such as anthracenes and cyclopentadiene have general use as excellent auxiliaries and ligands in asymmetric synthesis.