New synthetic routes toward enantiopure (2S,3R,4R)-4-hydroxyisoleucine by 1,3-dipolar cycloaddition of a chiral nitrone to C4 alkenes

被引：34

作者：

Aouadi, Kaiss

Jeanneau, Erwann

Msaddek, Moncef

Praly, Jean-Pierre

机构：

[1] Univ Lyon 1, CNRS, Inst Chim Biochim Mol Supramol, UMR5246,CEP Lyon, F-69622 Lyon, France

[2] Univ Monastir, Fac Sci, Lab Synth Heterocyclique, Monastir 5019, Tunisia

[3] Univ Lyon 1, Ctr Diffrattometr Henri Longchambon, F-69622 Villeurbanne, France

来源：

SYNTHESIS-STUTTGART | 2007年 / 21期

关键词：

chiral nitrone; 1,3-dipolar cycloaddition; isoxazolidines; stereocontrol; 4-hydroxyisoleucine;

D O I：

10.1055/s-2007-990802

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,3-Dipolar cycloaddition reaction of a chiral nitrone derived from (-)-menthone to E/Z mixtures of crotonaldehyde or (Z)-but-2-en-1,4-diol opens, by simultaneous creation of three contiguous asymmetric centers, new access to enantiopure (2S,3R,4R)-4-hydroxyisoleucine, respectively in 13% (7 steps) and 34% (6 steps) overall yield.

引用

收藏

页码：3399 / 3405

页数：7

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