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. 2010 Feb 3;132(4):1188-9.
doi: 10.1021/ja9069997.

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

Duncan J Wardrop  1 , Edward G Bowen, Raymond E Forslund, Adam D Sussman, Samanthi L Weerasekera
Affiliations

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

Duncan J Wardrop et al. J Am Chem Soc. .

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.

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References

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