Acylative kinetic resolution of racemic heterocyclic amines with (R)-2-phenoxypropionyl chloride

被引：13

作者：

Vakarov, Sergey A. ^{[1
]}

Gruzdev, Dmitry A. ^{[1
]}

Chulakov, Evgeny N. ^{[1
]}

Sadretdinova, Liliya Sh. ^{[1
]}

Tumashov, Andrey A. ^{[1
]}

Pervova, Marina G. ^{[1
]}

Ezhikova, Marina A. ^{[1
]}

Kodess, Mikhail I. ^{[1
,2
]}

Levit, Galina L. ^{[1
]}

Krasnov, Victor P. ^{[1
]}

Charushin, Valery N. ^{[1
,2
]}

机构：

[1] RAS, Postovsky Inst Organ Synth, Ural Branch, 22-20 S Kovalevskoy Akad Skaya St, Ekaterinburg 620990, Russia

[2] Ural Fed Univ, 19 Mira St, Ekaterinburg 620002, Russia

来源：

TETRAHEDRON-ASYMMETRY | 2016年 / 27卷 / 24期

基金：

俄罗斯科学基金会;

关键词：

DIASTEREOSELECTIVE ACYLATION; N-TOSYL-(S)-PROLYL CHLORIDE; EFFICIENT;

D O I：

10.1016/j.tetasy.2016.10.004

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The acylative kinetic resolution of racemic heterocyclic amines such as 3,4-dihydro-3-methyl-2H-[1,4] benzoxazines, 3,4-dihydro-3-methyl-2H-[1,4]benzothiazine, 2-methyl-1,2,3,4-tetrahydro-quinolines and 2-methylindoline with enantiopure (R)-2-phenoxypropionyl chloride has been studied. It has been found that acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzothiazine proceeds with the best stereoselectively when compared with other racemic amines. An efficient method for the preparation of (S)-3,4-dihydro-3-methyl-2H-[1,4]benzothiazine (99.4% ee) via a kinetic resolution protocol was developed. The possibility of recycling (R)-2-phenoxypropionic acid has been demonstrated. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：1231 / 1237

页数：7

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