1.
Org Lett
; 16(17): 4484-7, 2014 Sep 05.
Artigo
em Inglês
| MEDLINE
| ID: mdl-25134438
RESUMO
Novel C-ethoxycarbonyl cyclic ketonitrones are synthesized from the Ag- or Cu-catalyzed ring expansion of ß-diazo cyclic hydroxylamines. The latter are themselves easily obtained by the addition of lithiated ethyl diazoacetate onto cyclic nitrones. The regioselective metal-catalyzed rearrangement of ß-diazo cyclic hydroxylamines proved highly efficient and resulted in a synthetically useful ring expansion to produce 6- or 7-membered ring functionalized nitrones. The outcome of the two steps, i.e. nucleophilic addition of α-diazoesters to nitrones and ring expansion, is a formal nitrone homologation.