Diastereoselectivity in Mn(III)-promoted 4-exo-trig cyclization of enamides to beta-lactams

[reaction: see text] The effect of chiral substituents on the enamide nitrogen atom upon the diastereoselection of the Mn(III)-mediated 4-exo-trig cyclization to beta-lactams was studied. A significant level of diastereoselectivity was achieved when an amino acid ester moiety was included into the enamidic skeleton. The structure of the major diastereoisomer was suggested by semiempirical calculations.