Enantioselective access to five- and six-membered nitrogen-containing heterocycles, based on the asymmetric michael addition of chiral imines and chiral enamino esters

Article abstract of DOI:10.3987/COM-97-S(N)47

The addition reaction of chiral imines, (ent-10, 48, 70) and chiral enamino esters (52, 55, 73) with maleic anhydride (32), citraconic anhydride (57), α-chloroacrylonitrile (29), and nitroethylene (74), has been investigated. These condensations proved to be in general highly regio-, diastereo-, and enantioselective. In most cases the primary adducts underwent an in situ N-heterocyclization, allowing the enantioselective access to nitrogen-containing, five-and six-membered heterocycles.