Synthesis of β-hydroxy O-alkyl hydroxylamines from epoxides using a convenient and versatile two-step procedure

Abstract

A simple and convenient synthetic method was developed to prepare β-hydroxy O-alkyl hydroxylamines in which base-mediated ring opening of epoxides with acetophenone oxime followed by cleavage of the oxime with 2,4-dinitrophenylhydrazine in acidic media furnished the hydroxylamine, which can be protected in situ with various N-protecting groups. © Georg Thieme Verlag Stuttgart · New York.