The Journal of organic chemistry

Stereoselective cyclization reactions of IBX-generated alkoxyamidyl radicals

B Janza, A Studer

Index: Janza, Birgit; Studer, Armido Journal of Organic Chemistry, 2005 , vol. 70, # 17 p. 6991 - 6994

Full Text: HTML

Citation Number: 57

Abstract

In this paper, a method for the generation of alkoxyamidyl radicals is presented. These N- centered radicals can efficiently be formed starting from the corresponding acylated alkoxyamines using IBX as an oxidant. Stereoselective 5-exo and 6-exo reactions with these N-heteroatom-centered radicals leading to isoxazolidines and [1, 2] oxazinanes are discussed. The NO bond in the heterocycles can readily be cleaved with SmI2 to provide ...