α-Oxohydrazones as imine component in the synthesis of 4-functionalized azetidinones by the Staudinger reaction

1-(Methyl-p-tolyl-amino)-3-phenoxy-2-azetidinones 4-COX and 4-R substituted (COX: X=Me, Et, Ph, NMe2, NEt2, OBut; R=Me, Et, Ph) were smoothly prepared from the corresponding α-(methyl-p-tolyl)hydrazonylated ketones, amides and esters via [2+2] cycloaddition with phenoxyketene. The reaction was generally high-yielding and diastereoselective, leading to β-lactams with a cis relationship between the PhO and the COX moieties, except for R=Ph, where an opposite stereoselectivity was instead observed. The azetidinones represent interesting intermediates which couple protection at N(1) and functionalization at position 4 of the ring. Deprotection of N(1) can be easily attained by oxidative N–N cleavage with magnesium monoperoxyphthalate.