Abstract
An efficient enantioselective synthesis of 3-acetoxy trans-beta-lactams 7a and 7b via [2+2] cycloaddition reactions of imines 4a and 4b, derived from a polycyclic aromatic amine and bicyclic chiral acid obtained from (+)-car-3-ene, is described. The cycloaddition was found to be highly enantioselective, producing only trans-(3R,4R)-N-azetidin-2-one in very good yields. This is the first report of the synthesis of enantiomerically pure trans-beta-lactams 7a and 7b with a polycyclic aromatic substituent at N(1) of the azetidin ring.