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

被引：6
|
作者：
Pádár, P
Hornyák, M
Forgó, M
Kele, Z
Paragi, G
Howarth, NM
Kovács, L
机构：
[1] Univ Szeged, Dept Med Chem, H-6720 Szeged, Hungary
[2] Univ Szeged, Dept Organ Chem, H-6720 Szeged, Hungary
[3] Univ Szeged, Hungarian Acad Sci, Prot Chem Res Grp, H-6720 Szeged, Hungary
[4] Heriot Watt Univ, Sch Engn & Phys Sci, Edinburgh EH14 4AS, Midlothian, Scotland
来源：
TETRAHEDRON | 2005年 / 61卷 / 28期
基金：
英国惠康基金;
关键词：
1,3-dipolar cycloaddition; isoxazolidines; bicyclic 1,2-oxazepanes; 9-oxa-1-azabicyclo[4.2.1]nonanes; asymmetric synthesis;
D O I：
10.1016/j.tet.2005.04.066
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The intramolecular 1,3-dipolar cycloaddition of unsaturated nitrones derived front methyl alpha-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)center dot OEt2) on yields and diastereomeric ratios have been examined in detail. The best result (90% yield) was achieved when MgCl2 was present (in toluene, 120 degrees C bath temperature, 12 h). The stereoselectivity of the 1,3-dipolar cycloaddition was not significantly altered under the conditions investigated. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6816 / 6823
页数：8
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