New synthesis of chiral 1,3-oxazinan-2-ones from carbohydrate derivatives.

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.