Epimerisation of penicillanic acid derivatives and their rearrangement to 1,4-thiazepines: evidence for an E1cB mechanism
Abstract
A common enolate-like intermediate is implicated in the weak base-catalysed conversion of methyl 6β-phthalimidohomopenicillanate into methyl 6α-phthal-imidohomopenicillanate and methyl 2,3,4,7-tetrahydro-2,2-dimethyl-7-oxo-6-phthalimido-1,4-thiazepine-3(S)-acetate.