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

The intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived from methyl α- 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 (3 S,...

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Bibliographic Details
Published in:Tetrahedron 2005-07, Vol.61 (28), p.6816-6823
Main Authors: Pádár, Petra, Hornyák, Miklós, Forgó, Péter, Kele, Zoltán, Paragi, Gábor, Howarth, Nicola M., Kovács, Lajos
Format: Article
Language:English
Subjects:
1,3-Dipolar cycloaddition
9-Oxa-1-azabicyclo[4.2.1]nonanes
Asymmetric synthesis
Bicyclic 1,2-oxazepanes
Isoxazolidines
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Summary:The intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived from methyl α- 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 (3 S,4 R,5 S,6 S,8 S) configuration, determined by NMR spectroscopy]. The effects of different Lewis acid catalysts (MgCl 2, ZnCl 2 and BF 3·OEt 2) 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. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.04.066