Straightforward synthesis of enantiomerically pure (3S,4R)- and (3R,4S)-3,4-isopropylidenedioxypyrroline 1-oxide, precursors of functionalized cis-dihydroxy azaheterocycles, by a novel "one-pot" procedure

被引：36

作者：

Cicchi, S ^{[1
]}

Corsi, M ^{[1
]}

Brandi, A ^{[1
]}

Goti, A ^{[1
]}

机构：

[1] Univ Florence, CSCEA, Dipartimento Chim Organ Ugo Schiff, Ctr Studio CNR Chim & Struct Composti Eterociclic, I-50019 Florence, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 05期

关键词：

D O I：

10.1021/jo0157573

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantiomerically pure nitrone 3, a valuable precursor of mono- and bicyclic azaheterocycles, has been synthesized in 57% yield by a novel "one-pot" process starting from lactol 1, in turn readily available from D-arabinose. The same process, consisting of reaction with a O-silyl-protected hydroxylamine followed by mesylation in pyridine. furnished ent-3 in 55% yield when applied to L-arabinose.

引用

页码：1678 / 1681

页数：4

共 40 条

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