Heterocycles p. 2495 - 2514 (2004)
Update date:2022-08-02
Topics:
Davoli, Paolo
Spaggiari, Alberto
Ciamaroni, Elisa
Forni, Arrigo
Torre, Giovanni
Prati, Fabio
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.
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Doi:10.1016/j.jorganchem.2004.05.026
(2004)Doi:10.1021/ic50215a047
(1981)Doi:10.1021/jo0625958
(2007)Doi:10.1002/ejoc.202000089
(2020)Doi:10.1016/S0040-4020(01)91423-1
(1985)Doi:10.1016/j.bmcl.2006.11.083
(2007)