A Convergent Approach to Heterocycle Synthesis via Silver Ion Mediated α-Keto Imidoyl Halide-Arene Cyclizations. An Application to the Synthesis of the Erythrinane Skeleton

Article abstract of DOI:10.1021/jo00358a001

α-Keto imidoyl halides formed by the reaction of representative 2-phenylethyl and related isocyanides with acyl halides undergo facile cyclization induced by silver salts to provide the corresponding heterocycles in good to excellent yield.An efficient synthesis of the erythrinane skeletal system which relies upon the sequential utlization of this method followed by an azomethine ylide <3 + 2> cycloaddition reaction is described.