Abstract
Nitrous acid deaminations of threo-(Ia) and erythro-phenylserine methyl ester (Ib) gave methyl benzoylacetate (II) and methyl phenylmalonaldehydate (IX) by hydrogen migration and phenyl migration, respectively. Further reaction of IX afforded methyl α-hydroximinophenylacetates (IIIa-b) and N-nitrosooxazolidines (VIa-g). Deaminations of threo-(XIIIa) and erythro-phenylserine (XIIIb) were, however, highly specific and gave the corresponding α-acetoxy acid as the sole product with retention of configuration. The reaction paths involved in this study were discussed.
