TY - JOUR
T1 - Intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived from methyl α-d-glucopyranoside
AU - Pádár, Petra
AU - Hornyák, Miklós
AU - Forgó, Péter
AU - Kele, Zoltán
AU - Paragi, Gábor
AU - Howarth, Nicola M.
AU - Kovács, Lajos
PY - 2005/7/11
Y1 - 2005/7/11
N2 - 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.
AB - 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.
KW - 1,3-Dipolar cycloaddition
KW - 9-Oxa-1-azabicyclo[4.2.1]nonanes
KW - Asymmetric synthesis
KW - Bicyclic 1,2-oxazepanes
KW - Isoxazolidines
UR - http://www.scopus.com/inward/record.url?scp=20444433514&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2005.04.066
DO - 10.1016/j.tet.2005.04.066
M3 - Article
VL - 61
SP - 6816
EP - 6823
JO - Tetrahedron
JF - Tetrahedron
IS - 28
ER -