title: New synthesis of chiral 1,3-oxazinan-2-ones from carbohydrate derivatives.
abstract: Chiral 1,3-oxazinan-2-ones are useful intermediates in synthesizing pharmaceutical compounds and amino alcohols. In this paper, we report a new synthetic method to chiral 6-hydroxymethyl 1,3-oxazinan-2-ones and their analogues from carbohydrate derivatives. The synthesis was accomplished by the reaction of optically pure 3-hydroxy-gamma-butyrolactone with a primary amine to give an amide, which was reduced and carbonylated to give the desired compound class.
authors.affiliation: Department of Chemistry, University of New Orleans, New Orleans, Louisiana 70148, USA.
authors.forename: Jean-Rene
authors.initials: JR
authors.lastname: Ella-Menye
authors.forename: Vibha
authors.initials: V
authors.lastname: Sharma
authors.forename: Guijun
authors.initials: G
authors.lastname: Wang
mesh_terms: D015107:4-Butyrolactone / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D015195:Drug Design; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D000588:Amines; D000605:Amino Alcohols; D002241:Carbohydrates; D010078:Oxazines; D015107:4-Butyrolactone