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通过一种新颖的“一锅法”直接合成对映体纯的(3S,4R)-和(3R,4S)-3,4-异亚丙基二氧吡咯啉1-氧化物，即功能化顺式二羟基氮杂环的前体。

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.

作者信息

Cicchi Stefano, Corsi Massimo, Brandi Alberto, Goti Andrea

机构信息

Dipartimento di Chimica Organica Ugo Schiff, Centro di Studio C.N.R. sulla Chimica e la Struttura dei Composti Eterociclici e loro Applicazioni, Università degli Studi di Firenze, via della Lastruccia 13, I-50019 Sesto Fiorentino, Firenze, Italy.

出版信息

J Org Chem. 2002 Mar 8;67(5):1678-81. doi: 10.1021/jo0157573.

DOI:10.1021/jo0157573
PMID:11871902
Abstract

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.

摘要

对映体纯的硝酮3是单环和双环氮杂环的重要前体，它通过一种新颖的“一锅法”从乳糖醇1开始合成，产率为57%，而乳糖醇1又可从D-阿拉伯糖轻松制得。当将相同的过程应用于L-阿拉伯糖时，即与O-硅烷基保护的羟胺反应，然后在吡啶中进行甲磺酰化，得到对映体ent-3，产率为55%。

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