| abstract |
3β-Substituted succinimido)azetidinones represented by the formula ##STR1## wherein R and R 1 are e.g. C 1 -C 5 alkanoyloxy, benzoyloxy, substituted benzoyloxy, or benzyloxy, or one of R and R 1 is hydrogen and the other is as defined above; R 2 is C 1 -C 4 alkoxycarbonyl or an arylvinyl group e.g. styrryl or 2-furylvinyl; and R 3 is e.g. protected-carboxymethyl, or an NH protecting group; are provided via stereoselective cycloaddition of imines with chiral auxiliary 3,4-disubstituted succinimidoacetyl chlorides. The chiral auxiliary e.g., 3S,4S-dibenzoyloxy-and 3S,4S-diacetoxysuccinimidoacetyl chloride, is obtained from tartaric acid via anhydride and imide formation with retention of chirality. The chiral azetidinones obtained are useful intermediates to β-lactam antibacterial compounds. |