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Intramolecular oxamidation of unsaturated O-alkyl hydroxamates: a remarkably versatile entry to hydroxy lactams.

ABSTRACT: 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.

SUBMITTER: Wardrop DJ

PROVIDER: S-EPMC2812663 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

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Intramolecular oxamidation of unsaturated O-alkyl hydroxamates: a remarkably versatile entry to hydroxy lactams.

Wardrop Duncan J DJ Bowen Edward G EG Forslund Raymond E RE Sussman Adam D AD Weerasekera Samanthi L SL

Journal of the American Chemical Society 20100201 4

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. ...[more]

PMID: 19788297

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