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Org Lett. 2013 Jun 7;15(11):2888-91. doi: 10.1021/ol4012663. Epub 2013 May 22.

Nazarov reactions of vinyl cyclopropylamines: an approach to the imino-Nazarov problem.

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


Dichlorocyclopropanation of 2-amino-1,3-dienes affords 1-alkenyl-1-amino-2,2-dichlorocyclopropanes which undergo silver-assisted 2-π electrocyclic opening to furnish 3-aminopentadienyl cations. Nazarov-type cyclization of these intermediates leads to cyclopentenone iminium salts, which provide allylic amines upon reduction. This process, the imino version of the traditional Nazarov reaction, can also be combined with an interrupted Nazarov domino process to give polycyclic amines.

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