Intra-molecular nitrone–olefin cycloaddition of d-glucose derived allylic alcohol: synthesis of new aminocyclohexitols

Abstract

Diastereo- and regioselelective intra-molecular nitrone–olefin cycloaddition reaction of in situ generated N-benzylnitrones, obtained from d-glucose derived precursors 5a/ 5b furnished dihydroxy functionalized isoxazolidines. The N– O bond reductive cleavage and removal of N/ O-benzyl groups led to the formation of stereochemically well defined aminocyclohexitols.