A novel fragmentation of the. beta.-lactam ring: stereoselective entry to vinyl ethers by reaction of N-(arylidene (or alkylidene) amino)-2-azetidinones with ozone

B Alcaide, M Miranda, J Perez-Castells…

Index: Alcaide, Benito; Miranda, Miguel; Perez-Castells, Javier; Sierra, Miguel A. Journal of Organic Chemistry, 1993 , vol. 58, # 2 p. 297 - 298

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Citation Number: 19

Abstract

Benito Alcaide,' Miguel Miranda, Javier PCez-Castells, and Miguel A. Sierra ... Departamento de Qulmica Orgtinica I, Facultad de Qulmica, Universidad Complutenae, 28040-Madrid, Spain ... Summary: The title compounds undergo a novel 2-aze- tidinone ring fragmentation by reaction with ozone fol- lowed by NaBH4 workup to stereoselectively yield vinyl ethers via intermediate N-nitroso-8-lactams. The strained @-lactam ring renders these fascinating molecules ...