Analogues of insulin secretagogue (2S,3R,4S)-4-hydroxyisoleucine:: synthesis by 1,3-dipolar cycloaddition reactions of chiral nitrones to alkenes

被引：33
|
作者：
Aouadi, Kaiss [1 ]
Jeanneau, Erwann [2 ]
Msaddek, Moncef [3 ]
Praly, Jean-Pierre [1 ]
机构：
[1] Univ Lyon, Inst Chim & Biochim Mol & Supramol, CNRS,UMR 5246, CPE Lyon,Lab Chim Organ 2, F-69622 Villeurbanne, France
[2] Univ Lyon, Ctr Diffrattometr Henri Longchambon, F-69622 Villeurbanne, France
[3] Univ Monastir, Lab Synth Heterocycl Chim Subst Nat, Fac Sci Monastir, Monastir 5000, Tunisia
来源：
TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 09期
关键词：
D O I：
10.1016/j.tetasy.2008.04.006
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
(2S,3R,4S)-4-Hydroxyisoleucine, found in fenugreek, is an insulin secretagogue molecule. Non-natural analogues of (2S,3R,4R)- and (2R,3S,4S)-4-hydroxyisoleucine were efficiently prepared by 1,3-dipolar cycloaddition reactions of chiral nitrones derived from either (-)- or (+)-menthone to alkenes. The cycloadducts, obtained via the exo-approach of the alkenes to the nitrone's less hindered face, led after a reductive step and cleavage of the chiral auxiliary, to enantiopure non-natural amino acids in good overall yield. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1145 / 1152
页数：8
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