Intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived from methyl α-d-glucopyranoside

Petra Pádár, Miklós Hornyák, Péter Forgó, Zoltán Kele, Gábor Paragi, Nicola M. Howarth, Lajos Kovács

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7 Citations (Scopus)

Abstract

The intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived from methyl a-d-glucopyranoside with 2-furaldehyde has been studied. This cycloaddition was found to afford three 9-oxa-1-azabicyclo[4.2.1] nonane diastereomers in a 3:1:1 ratio [with the principal isomer possessing a (3S,4R,5S,6S,8S) configuration, determined by NMR spectroscopy]. The effects of different Lewis acid catalysts (MgCl2, ZnCl2 and BF 3·OEt2) on yields and diastereomeric ratios have been examined in detail. The best result (90% yield) was achieved when MgCl 2 was present (in toluene, 120°C bath temperature, 12 h). The stereoselectivity of the 1,3-dipolar cycloaddition was not significantly altered under the conditions investigated. © 2005 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)6816-6823
Number of pages8
JournalTetrahedron
Volume61
Issue number28
DOIs
Publication statusPublished - 11 Jul 2005

Keywords

  • 1,3-Dipolar cycloaddition
  • 9-Oxa-1-azabicyclo[4.2.1]nonanes
  • Asymmetric synthesis
  • Bicyclic 1,2-oxazepanes
  • Isoxazolidines

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