Synthesis of enantiomerically pure 4-polyfluoromethyl-4-hydroxy-homoprolines by intramolecular cyclization of 6-amino-5-polyfluoromethyl-hex-2-enoic acids

被引：5

作者：

Shaitanova, Elena N. ^{[1
]}

Gerus, Igor I. ^{[1
]}

Kukhar, Valery P. ^{[1
]}

Haufe, Guenter ^{[2
]}

机构：

[1] Natl Acad Sci Ukraine, Inst Bioorgan Chem & Petrochem, UA-02094 Kiev, Ukraine

[2] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2014年 / 160卷

关键词：

Fluorinated amino acids; Cyclization; Homoprolines; Enones; GABA uptake inhibitors; STEREOSELECTIVE-SYNTHESIS; MICHAEL ADDITION; GABA-UPTAKE; BIOLOGICAL EVALUATION; AMINO-ACIDS; CLONING;

D O I：

10.1016/j.jfluchem.2014.01.001

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An effective route to racemic and enantiopure 4-polyfluoromethyl-4-hydroxy-homoprolines was developed based on readily available 2-alkoxyvinyl-polyfluoromethyl ketones. Key step of the synthesis was a diastereoselective heterocyclization of 6-amino-5-polyfluoromethyl-hex-2-enoic acids under acidic conditions. The absolute configuration of the stereogenic centers was determined by X-ray. (C) 2014 Elsevier B.V. All rights reserved.

引用

页码：8 / 11

页数：4

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