Intramolecular oxyacetoxylation of N allylamides: an expeditious synthesis of oxazolines and oxazines by using a PhI(OAc)2/hydrogen fluoride pyridine system.
The synthesis of oxazolines and oxazines from N allylamides was accomplished via an unprecedented reaction set. This reaction involved an intramolecular cyclization of N allylamides resulting from nucleophilic attack of the allylamine on the benzoxazin 4 one. Unlike the previous literature, the isolable N allylamide could readily be subjected to exo and endo fashion ring closure under conditions to afford the title compounds.
Organic biomolecular chemistry