Issue 23, 1994

N-alkenyl nitrone dipolar cycloaddition routes to piperidines and indolizidines. Part 7. Hydroxylamine–alkyne cyclisations. Formation of cyclic nitrones and application to the synthesis of the proposed structure for (±)-acacialactam

Abstract

The cyclisation of the alkynylhydroxylamines 2, 13, 14, 19, 27, 34, 39, 46 and 47 to give five-, six- and seven-membered cyclic nitrones is described. A concerted intramolecular ene-like pathway is proposed for the addition of the N–O–H group across the triple bond. Using the nitrone 48 as the starting material, the seven-membered lactam structure 49 proposed for the natural product acacialactam was prepared and was found to be incorrect.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1994, 3379-3395

N-alkenyl nitrone dipolar cycloaddition routes to piperidines and indolizidines. Part 7. Hydroxylamine–alkyne cyclisations. Formation of cyclic nitrones and application to the synthesis of the proposed structure for (±)-acacialactam

M. E. Fox, A. B. Holmes, I. T. Forbes and M. Thompson, J. Chem. Soc., Perkin Trans. 1, 1994, 3379 DOI: 10.1039/P19940003379

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