A novel carbonyl transposition reaction led by aromatic amines nucleophilic addition to \{2 oxo glycoside\} was discovered. The mechanism of the reaction was provided through tracing the change of 1H NMR of a hemiacet...A novel carbonyl transposition reaction led by aromatic amines nucleophilic addition to \{2 oxo glycoside\} was discovered. The mechanism of the reaction was provided through tracing the change of 1H NMR of 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, 13 C NMR, 1H 1H COSY and 1H 13 C COSY spectra. 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.展开更多
文摘A novel carbonyl transposition reaction led by aromatic amines nucleophilic addition to \{2 oxo glycoside\} was discovered. The mechanism of the reaction was provided through tracing the change of 1H NMR of 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, 13 C NMR, 1H 1H COSY and 1H 13 C COSY spectra. 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.
