Synthesis of enantiopure carbohydrate mimetics by Lewis acid catalyzed rearrangement of 1,3-dioxolanyl-substituted 1,2-oxazines

被引：81

作者：

Al-Harrasi, A ^{[1
]}

Reissig, HU ^{[1
]}

机构：

[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 38期

关键词：

carbohydrates; heterocycles; rearrangement; reduction;

D O I：

10.1002/anie.200501127

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Under control: Lewis acids induce an unexpected rearrangement of 1,3-dioxolanyl-substituted 1,2-oxazines to provide bicyclic compounds in a stereocontrolled manner. They are precursors for enantiopure carbohydrate mimetics containing 3-aminotetrahydropyran or 4-aminooxepane substructures (see scheme; Bn = benzyl). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6227 / 6231

页数：5

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