Radical 4??exo Cyclizations onto O??Alkyloxime Acceptors: Towards the Synthesis of Penicillin??Containing Antibiotics
EM Scanlan, JC Walton
Index: Scanlan, Eoin M.; Walton, John C. Helvetica Chimica Acta, 2006 , vol. 89, # 10 p. 2133 - 2143
Full Text: HTML
Citation Number: 14
Abstract
Abstract The 4-exo cyclizations of two types of carbamoyl radicals onto O-alkyloxime acceptor groups were studied as potential routes to 3-amino-substituted azetidinones and hence to penicillins. A general synthetic route to 'benzaldehyde oxime oxalate amides'(= 2- [(benzylideneamino) oxy]-2-oxoacetamides; see, eg, 10c) of 2-{[(benzyloxy) imino] methyl}- substituted thiazolidine-4-carboxylic acid methyl esters 9 was developed (Scheme 3). It ...
Related Articles:
Phosphonium salt-catalysed synthesis of nitriles from in situ activated oximes
[Denton, Ross M.; An, Jie; Lindovska, Petra; Lewis, William Tetrahedron, 2012 , vol. 68, # 13 p. 2899 - 2905]
Preparation of β-and γ-lactams from carbamoyl radicals derived from oxime oxalate amides
[Scanlan, Eoin M.; Slawin, Alexandra M.Z.; Walton, John C. Organic and Biomolecular Chemistry, 2004 , vol. 2, # 5 p. 716 - 724]