Preparation of N-glycosylhydroxylamines and their oxidation to nitrones for the enantioselective synthesis of isoxazolidines

被引：34

作者：

Cicchi, S ^{[1
]}

Marradi, M ^{[1
]}

Corsi, M ^{[1
]}

Faggi, C ^{[1
]}

Goti, A ^{[1
]}

机构：

[1] Univ Florence, Dipartimento Chim Organ Ugo Schiff, I-50019 Florence, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 21期

关键词：

hydroxylamines; sugars; nitrones; chiral auxiliaries; enantioselectivity;

D O I：

10.1002/ejoc.200300353

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-benzyl- and N-methyl-N-glycosylhydroxylamines 3a-i were conveniently obtained by reaction of sugars with N-substituted hydroxylamines according to a novel procedure. Subsequent oxidation occurred at the alkyl group, selectively affording the corresponding C-phenyl- and C-unsubstituted N-glycosylnitrones. C-phenyl-N-glycosylnitrones 10 and 13 under-went highly stereoselective 1,3-dipolar cycloaddition with dimethyl maleate, with the sugar moiety acting as a chiral auxiliary. Final removal of the glycosyl moiety afforded enantiopure enantiomeric isoxazolidines 17 and ent-17 which are oxa-analogues of proline diester derivatives. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

引用

页码：4152 / 4160

页数：9

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