Synthesis of (2S,3R)[3-2H1]- and (2S,3S)[2,3-2H2]-serines and (1R)[1-2H1]- and (1S,2RS)[1,2-2H2]-2-aminoethanols

Abstract

(2S,3R)[3-²H₁]-and (2S,3S)[2,3-²H₂]-serines have been prepared by a route which includes a Baeyer–Villiger oxidation involving rearrangement of a secondary chiral centre; a ¹H n.m.r. assay has been developed to assess stereochemical integrity of both prochiral centres in 2-aminoethanol and this shows that decarboxylation of each sample of serine proceeds without loss of chirality at C-3, yielding (1R)[1-²H₁]-and (1S,2RS)-[1,2-²H₂]-2-aminoethanols, respectivsely.