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Highly diastereoselective N-acyliminium ion cyclization reactions of a tethered furan

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


The acid catalysed cyclization reactions of tethered furan-4,5- dihydroxypyrrolid-2-ones and furan-4,5-diacetoxypyrrolid-2-ones, via their corresponding N-acyliminium ion intermediates, have been studied. In the case of the tethered furan-3,4-dihydroxypyrrolid-2-one 16, having a two carbon tether, the linearly fused tricyclic compound 18 was formed with high cis selectivity (cis/trans=84:16) when BF3·OEt2 was used as a catalyst. However, when the cyclization reaction was carried out on the...[Show more]

CollectionsANU Research Publications
Date published: 2012
Type: Journal article
Source: Tetrahedron
DOI: 10.1016/j.tet.2012.10.014


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