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

页码：4817 / 4821

页数：5

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