Abstract: Anovel carbonyl transposition reaction led by aromatic amine's nucleophilic addition to 2 oxo glycoside was discovered. The mechanism of the reaction was provided through tracing the change of ¹H NMRof a hemiacetal intermediate which was obtained in the reaction of o phenylene diamine with 2-oxo-glycoside. Both the intermediate and the product were identified by FTIR, ¹H NMR, ¹³C NMR, ¹H₁H-COSYand ¹H₁₃ C COSYspectra. The other aromatic amines' reaction with 2-oxo-glycoside also proved the mechanism. This reaction provides a new method for preparing 2-deoxy-2-aromatic amino 3-oxo-glycosides, which is a new kind of material used in assymetric synthesis.

Key words: 2-Oxo glycoside, Carbonyl transposition reaction, Aromatic amine, Amino sugar, Assymetric synthesis