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

作者: Duncan J. Wardrop , Edward G. Bowen , Raymond E. Forslund , Adam D. Sussman , Samanthi L. Weerasekera

DOI: 10.1021/JA9069997

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摘要: The development of a versatile method for the preparation five- to eight-membered hydroxy lactams that involves iodine(III)-mediated oxamidation unsaturated O-alkyl hydroxamates is described. This transformation, which believed proceed through intermediacy singlet nitrenium and bicyclic N-acyl-N-alkoxyaziridinium ions, both stereospecific highly regioselective in most 22 cases examined.

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