Diastereoselective synthesis of α-methyl and α-hydroxy-β- amino acids via 4-substituted-1,3-oxazinan-6-ones

Abstract

(Chemical Equation Presented) 1,3-Oxazinan-6-ones have been utilized in a series of enolate reactions to produce 5-hydroxy and 5-alkyl-4-substituted-1,3- oxazinan-6-ones with excellent trans diastereoselectivity. Highlighting the versatility of the oxazinanone, a number of transformations were performed to produce a variety of protected N-H and N-methyl α-hydroxy- and α-methyl-β-amino acids. © 2007 American Chemical Society.