N-Cyanomethyl-β-chloro amines:: chiral building blocks for the synthesis of azacrown ethers

被引：4
|
作者：
Couty, Francois [1 ]
Evano, Gwilherm [1 ]
Menguy, Laurence [1 ]
Steimetz, Vincent [1 ]
Toumi, Mathieu [1 ]
机构：
[1] Univ Versailles, CNRS, UMR 8180, Inst Lavoisier, F-78035 Versailles, France
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 28期
关键词：
D O I：
10.1016/j.tetlet.2006.05.046
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(1R,2S)-Ephedrine and norephedrine derived N-cyanomethyl-beta-chloro amines react with tri-, tetra- and penta-ethylene glycol to stereoselectively give the corresponding amino ethers. Further transformation into chiral monoaza 12-, 15- and 18-crown-4, -5 and -6 ethers was realized in three steps and good overall yields by: (i) mesylation, (ii) deprotection of the N-cyanomethyl group and (iii) intramolecular alkylation. Binding affinities of these azacrown ethers for alkali cations was studied by FAB-MS. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4817 / 4821
页数：5
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