Cleavage of the N(1)C(4) bond of 4-(4′-hydroxyphenyl)-azetidine-2-ones via quinone methide intermediates

β-Lactams: Versatile Building Blocks for the Stereoselective Synthesis of Non-β-Lactam Products

“…The β-alkoxy acid derivative 585 has been prepared from β-lactam 586 by treatment with sodium methoxide in methanol. 163 Dienic amino acid derivatives 588-590 were prepared from cyclobutane-fused lactams 591 by methanolysis, hydrolysis, or reduction (Scheme 190). 164 The starting lactams 591 were obtained in good yields from the commercially available 2-hydroxypyridine in one step, in aqueous solution, through a photochemical electrocyclic reaction.…”

“…The β-alkoxy acid derivative 585 has been prepared from β-lactam 586 by treatment with sodium methoxide in methanol . Formation of this compound has been explained by phenolate formation followed by rearrangement to an intermediate quinone methide 587 with concomitant cleavage of the N1−C4 β-lactam bond (Scheme ).…”