Selective Oxidation of Polyfunctional 2-Amino-1,3-propanediol Derivatives

摘要

Oxidation of polyfunctional threo-(1S,2S)-2-amino-1,3-propanediol derivatives with a 717 anion-ex-change resin-supported bromine has been investigated. The result showed that oxidized products were in close relationship with the substituents at nitrogen in the starting materials. Its primary and secondary amine derivatives were oxidized in the presence of Na_2HPO_4 to give essentially a substituted chiral oxazoline or C(3)-O acylated product in high yield, while oxidation of its N,N-dimethyl derivative mainly gave a chiral N-methyl oxidation-formylation product. This selective oxidation was first observed in 2-amino-1,3-propanediol chemistry.