Journal of Organic Chemistry p. 3546 - 3550 (1992)
Update date:2022-08-03
Topics:
Gasparski, Catherine M.
Ghosh, Arun
Miller, Marvin J.
A general procedure for the conversion of α-oximido-β-keto esters into vivinal tricarbonyl moieties by TiCl3 in aqueous, buffered (pH 5) conditions with acetone cosolvent was demonstrated.As applied to N-hydroxy β-lactam 17, which contained an α-oximido-β-keto ester side chain, these combined reductive and hydrolytic conditions effected simultaneous tricarbonyl formation and β-lactam N-O bond reduction.Vicinal tricarbonyl-containing N-unsubstituted β-lactam 18 was a direct precursor to semifunctionalized carbacephem 1.
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