Journal of the American Chemical Society · 2009 · 135 citations · 10 references
Natural SciencesChemistryMedicinal ChemistryDrug DiscoveryOrganic ChemistrySynthetic Medicinal ChemistryHeterocyclic ChemistryRetrosynthetic AnalysisLactam Synthesis
The development of a versatile method for the preparation of five- to eight-membered hydroxy lactams that involves the iodine(III)-mediated oxamidation of unsaturated O-alkyl hydroxamates is described. This transformation, which is believed to proceed through the intermediacy of singlet nitrenium and bicyclic N-acyl-N-alkoxyaziridinium ions, is both stereospecific and highly regioselective in most of the 22 cases examined.
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