Synthesis of chiral benzoxa(thia)zepine and pyridoxazepine derivatives using palladium-catalyzed intramolecular aryl amination reaction

摘要

A palladium-catalyzed method employing different bulky biaryl phosphanes as ligands has been developed for the intramolecular amination of aryl bromides and iodides. A variety of aryl halide substrates have been aminated through the intramolecular pathway in good yield using different sugar-derived amines to give furo-benzoxa(thia)zepine and pyridoxazepine derivatives. The method is capable of furnishing chiral, enantiopure benzoxa(thia)zepines and pyridoxazepines of significant biological importance. An efficient route to furo-benzoxa(thia)zepine and pyridoxazepine by a palladium-catalyzed intramolecular aryl amination has been reported using a D-glucose-derived substrate. One of the products has been converted to a chiral benzoxazepine derivative.