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Synthesis of spirocyclic azacycles from the cyclization of furan tethered N-acyliminium ions

Shengule, Sudhir R; Willis, Anthony; Pyne, Stephen G


The protic and Lewis acid promoted cyclization reactions of tethered furan-4,5-dihydroxypiperid-2-ones, furan-4,5-diacetoxypiperid-2-ones and furan-3,4-diacetoxypyrrolid-2-ones, via their corresponding N-acyliminium ion intermediates, have been studied. In the case of the furan-4,5-dihydroxypiperid- 2-one 2a and its diacetate derivative 2b, macrocyclic products were formed from an initial intermolecular reaction between 2a or 2b, via the nucleophilic C5 furan carbon, and their corresponding...[Show more]

CollectionsANU Research Publications
Date published: 2012
Type: Journal article
Source: Tetrahedron
DOI: 10.1016/j.tet.2011.11.055


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