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Org Lett. 2011 Jan 7;13(1):114-7. doi: 10.1021/ol102651k. Epub 2010 Dec 3.

Intermolecular [3 + 3]-cycloadditions of azides with the Nazarov intermediate.

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1
Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB, T6G 2G2, Canada.

Abstract

Tetrasubstituted 1,4-dien-3-ones undergo Nazarov cyclization at low temperature, followed by reaction with organic azides via an apparent [3 + 3]-cycloaddition to give bridged bicyclic triazenes. These products do not appear to be intermediates in the previously described Schmidt-type process to furnish dihydropyridones. The reaction typically occurs with high diastereoselectivity.

PMID:
21126097
DOI:
10.1021/ol102651k
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