Cycloaddition reactions on activated exo-glycals

被引：41

作者：

Enderlin, G

Taillefumier, C

Didierjean, C

Chapleur, Y

机构：

[1] Univ Nancy 1, CNRS, UMR 7565, Grp SUCRES, F-54506 Vandoeuvre Les Nancy, France

[2] Univ Nancy 1, CNRS, UMR 7036,Grp Biostruct, Inst Chim & Phys Mol & Biomol, F-54506 Vandoeuvre Les Nancy, France

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 14期

关键词：

D O I：

10.1016/j.tetasy.2005.06.027

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Cycloaddition reactions of activated exo-glycals and nitrones proceeded only under microwave activation, with excellent facial selectivities on furanoglycosylidenes and good stereocontrol on the nitrone producing only two diastereomeric spiroisoxazolidines. alpha/beta-Spiro sugar-isoxazolidines are obtained from pyrano exo-glycals. The cycloaddition reaction with nitrile oxide proceeds at room temperature and gives open-chain isoxazoles due to facile beta-elimination of the sugar ring oxygen on the intermediate isoxazoline ring system. All the heterocycles obtained this way can be regarded as nucleoside analogues. (C) 2005 Elsevier Ltd. All rights reserved.

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页码：2459 / 2474

页数：16

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