Preparation and 1,3-dipolar cycloadditions of chiral nitrones derived from D-xylose with vinyl acetate

被引：21
作者：
Fischer, R
Drucková, A
Fisera, L [1 ]
Hametner, C
机构：
[1] Slovak Univ Technol Bratislava, Dept Organ Chem, SK-81237 Bratislava, Slovakia
[2] Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria
来源：
ARKIVOC | 2002年
关键词：
chiral; dipolar cycloadditions; nitrones; isoxazolidines; saccharides;
D O I：
10.3998/ark.5550190.0003.810
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New chiral nitrones 8 and 13, easily prepared from D-xylose by multistep synthetic routes, undergo regioselective 1,3-dipolar cycloadditions with vinyl acetate giving 5-acetoxy isoxazolidines in good yields. Attack of the dipolarophile on the Z-configuration of the nitrone through an endo transition state from both prochiral faces of the nitrone affords C-3/C-5 trans isoxazolidines possessing C-1'/C-3 erythro (from si) and the C-1'/C-3 threo (from re) relative configuration as two major isomers.
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收藏
页码：80 / 90
页数：11
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