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

Journal Article


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 BF 3·OEt 2 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. © 2012 Elsevier Ltd. All rights reserved.

UOW Authors


  •   Shengule, Sudhir R. (external author)
  •   Ryder, Greg (external author)
  •   Willis, Anthony C. (external author)
  •   Pyne, Stephen

Publication Date


  • 2012

Citation


  • 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.

Scopus Eid


  • 2-s2.0-84869094990

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/4711

Has Global Citation Frequency


Number Of Pages


  • 5

Start Page


  • 10280

End Page


  • 10285

Volume


  • 68

Issue


  • 50

Place Of Publication


  • United Kingdom

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 BF 3·OEt 2 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. © 2012 Elsevier Ltd. All rights reserved.

UOW Authors


  •   Shengule, Sudhir R. (external author)
  •   Ryder, Greg (external author)
  •   Willis, Anthony C. (external author)
  •   Pyne, Stephen

Publication Date


  • 2012

Citation


  • 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.

Scopus Eid


  • 2-s2.0-84869094990

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/4711

Has Global Citation Frequency


Number Of Pages


  • 5

Start Page


  • 10280

End Page


  • 10285

Volume


  • 68

Issue


  • 50

Place Of Publication


  • United Kingdom