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

RIS ID

72809

Publication Details

Shengule, S. R., Ryder, G., Willis, A. C. & Pyne, S. G. (2012). Highly diastereoselective N-acyliminium ion cyclization reactions of a tethered furan. Tetrahedron, 68 (50), 10280-10285.

Abstract

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 related tethered furan–4,5-diacetoxypyrrolid-2-one 17, the linearly fused tricyclic compound 20 was formed as a single diastereoisomer with trans selectivity. In contrast, the attempted cyclization of the tethered furan–4,5-dihydroxypyrrolid-2-one 26, having a one carbon tether, did not result in formation of the corresponding linearly fused tricyclic system, instead it formed the dimer 29 as a single diastereoisomer. Cyclization reactions of the related tethered furan–4,5-diacetoxypyrrolid-2-one 27 also failed to give the corresponding linearly fused tricyclic system or macrocycle.

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Link to publisher version (DOI)

http://dx.doi.org/10.1016/j.tet.2012.10.014