SYNTHESIS OF HOMOCHIRAL 3-OXA-2,7-DIAZABICYCLO[3.3.0]OCTANES FROM AMINO-ACIDS BY INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION OF NITRONES

被引：33

作者：

AURICH, HG

FRENZEN, G

GENTES, C

机构：

[1] Fachbereich Chemie, Universität Marburg, Marburg, W-3550, Hans-Meerwein-Straße

来源：

CHEMISCHE BERICHTE-RECUEIL | 1993年 / 126卷 / 03期

关键词：

HETEROBICYCLO[3.3.0]OCTANES; HOMOCHIRAL; AMINO ACIDS; NITRONES; CYCLOADDITIONS; DIASTEREOSELECTIVE; INTRAMOLECULAR;

D O I：

10.1002/cber.19931260333

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Allylamino alcohols 0 were prepared from amino acids by various methods. Swern oxidation of 9 afforded aldehydes 11. By reaction of 11 with N-alkylhydroxylamines nitrone intermediates 4 were formed which spontaneously underwent an intramolecular 1,3-dipolar cycloaddition to yield the bicyclic compounds 6. The cycloaddition proceeds diastereoselectively furnishing homochiral compounds 6 from homochiral starting materials. The structure of 6aA was confirmed by X-ray structural analysis.

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页码：787 / 795

页数：9

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