Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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

Abstract

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.