Optically pure aminopolyols and polyoxamic acid derivatives from aziridine-2-carboxylates

Various new chiral building blocks could easily be prepared from optically pure cis and trans ethyl 3-(1',3'-dioxolan-4'-yl)aziridine-2-carboxylates. A stereochemically pure 1,3-dioxolan in the allyl position of an alpha-brom oacrylate induced a high (3R*,4'S*) selectivity in the Michael addition wit h an amine. After oxygen at the inducing centre was exchanged with nitrogen bearing a bulky substituent, the directing influence of this new group was examined. Solvent erects influencing the cis/trans ratio of aziridine form ation are discussed.