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

页码：6816 / 6823

页数：8

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