Lewis acid-promoted synthesis and reactivity of beta-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.
Dipartimento di Chimica G. Ciamician, Università degli Studi di Bologna, via Selmi 2, 40128-Bologna, Italy.
Giuliana
G
Cardillo
Luca
L
Gentilucci
Valeria
V
De Matteis