Lewis acid-promoted synthesis and reactivity of β-O-benzylhydroxylamino imides derived from D-glyceraldehyde

This paper describes the synthesis and use of beta-hydroxylamino imides derived from D-glyceraldehyde possessing a number of reactive sites that operate synergistically or alternatively to bring about highly regio- and diastereoselective transformations to give an optically pure aziridine-2-imide, a dihydro pyrimidine-2,4-dione, or a lactone. Both the syntheses, via the diastereoselective 1,4-conjugate addition of O-benzyl hydroxylamine to alpha,beta-unsaturated imides, and transformations can be simply tuned by choosing between different Lewis acids.