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.

Aluminum-Controlled Reactivity and Diastereoselectivity toward Radical Reactions of Optically Active Aldimines with Metallic Samarium

“…This method represents the first example of the dimerization of imines with Sm based on the chelation control of aluminum for the N -benzylideneamino alcohol radical. Optically active amino alcohols have been extensively used as catalysts in alkylation of aldehyde with alkyllithium or dialkylzinc, reduction of ketones with borane or borates, and dihydroxylation of a double bond with osmium tetraoxide . We are trying now to use our C 2 -chiral compounds for these reactions as asymmetric ligands.…”