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Paper | Regular issue | Vol 63, No. 11, 2004, pp.2495-2514
Published online, 17th September, 2004
DOI: 10.3987/COM-04-10166
Synthesis of N-Bridgehead Fused Bicyclic β-Lactams through Organometal-mediated Transformations of 1,2-Dialkenylaziridines

Paolo Davoli, Alberto Spaggiari, Elisa Ciamaroni, Arrigo Forni, Giovanni Torre, and Fabio Prati*

*Dipartimento di Chimica, Università di Modena e Reggio Emilia, via Campi 183, I- 41100 Modena, Italy


N-Bridgehead fused bicyclic β-lactams have been synthesized through sequential organometal-mediated transformations of 1,2-dialkenylaziridines, namely Co2(CO)8-catalysed carbonylation and ring-closing metathesis (RCM). When firstly subjected to RCM conditions, either with Schrock-Hoveyda or Grubbs’ catalyst, 1,2-dialkenylaziridines did not afford the expected bicyclic N-bridgehead products. In contrast, however, cis-1,2-dialkenylaziridines were amenable to carbonylative ring expansion, affording trans-1,4-dialkenyl-β-lactams which could be subsequently metathesized to the corresponding fused bicyclic compounds using Grubbs’ catalyst. Unexpectedly, carbonylation of trans-1,2-dialkenylaziridines occurred with the unprecedented rearrangement to the 5,6-dihydro-4H-[1,3]oxazine skeleton.