Stereoselective access to the versatile 4-aminohex-5-ene-1,2,3-triol pattern

被引：12

作者：

Ayad, T ^{[1
]}

Faugeroux, V ^{[1
]}

Génisson, Y ^{[1
]}

André, C ^{[1
]}

Baltas, M ^{[1
]}

Gorrichon, L ^{[1
]}

机构：

[1] Univ Toulouse 3, CNRS, UMR 5068, Lab Synth & Physicochim Mol Interet Biol, F-31062 Toulouse 04, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 25期

关键词：

D O I：

10.1021/jo048766v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed a stereocontrolled route allowing potential access to the eight isomers of 4-benzylaminohex-5-ene-1,2,3-triol in two or four steps and ca. 50% yield from readily available chiral nonracemic cis- or trans-alpha,beta-epoxyimine precursors. A new (NH4)(2)CO3-based carboxylation/intramolecular cyclization sequence allowed regio- and stereocontrolled C-3 epoxide opening while neat C-2 hydrolysis was ensured by simple aqueous acidic treatment.

引用

页码：8775 / 8779

页数：5

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