Stereoselective cyclization reactions of IBX-generated alkoxyamidyl radicals.
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 N-O bond in the heterocycles can readily be cleaved with SmI(2) to provide N-acylated 1,3-amino alcohols.
Janza
Birgit
B
Organisch-Chemisches Institut, Westfälische-Wilhelms-Universität, Corrensstrasse 40, 48149 Münster, Germany. studer@uni-muenster.de
Studer
Armido
A