Asymmetric Michael Addition in Synthesis of β-Substituted GABA Derivatives

被引：23

作者：

Han, Jianlin ^{[1
]}

Escorihuela, Jorge ^{[2
]}

Fustero, Santos ^{[2
]}

Landa, Aitor ^{[3
]}

Soloshonok, Vadim A. ^{[3
,4
]}

Sorochinsky, Alexander ^{[5
]}

机构：

[1] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat F, Nanjing 210037, Peoples R China

[2] Univ Valencia, Dept Quim Organ, Burjassot 46100, Spain

[3] Univ Basque Country UPV EHU, Fac Chem, Dept Organ Chem 1, Paseo Manuel Lardizabal 3, San Sebastian 20018, Spain

[4] Basque Fdn Sci, Ikerbasque, Alameda Urquijo 36-5,Plaza Bizkaia, Bilbao 48011, Spain

[5] Natl Acad Sci Ukraine, VP Kukhar Inst Bioorgan Chem & Petrochem, 1 Murmanska Str, UA-02094 Kiev, Ukraine

来源：

MOLECULES | 2022年 / 27卷 / 12期

基金：

中国国家自然科学基金;

关键词：

pharmaceuticals; neurological drugs; gamma-aminobutyric-acid derivatives; asymmetric Michael addition; chiral auxiliaries; enantioselective organocatalysis; chiral metal-ligand complexes; DIPHENYLPROLINOL SILYL ETHER; PRIMARY AMINE-THIOUREAS; ACID HALF-THIOESTERS; ONE-POT SYNTHESIS; CONJUGATE ADDITION; SELF-DISPROPORTIONATION; 1,3-DICARBONYL COMPOUNDS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; POLYKETIDE SYNTHASES;

D O I：

10.3390/molecules27123797

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

gamma-Aminobutyric acid (GABA) represents one of the most prolific structural units widely used in the design of modern pharmaceuticals. For example, beta-substituted GABA derivatives are found in numerous neurological drugs, such as baclofen, phenibut, tolibut, pregabalin, phenylpiracetam, brivaracetam, and rolipram, to mention just a few. In this review, we critically discuss the literature data reported on the preparation of substituted GABA derivatives using the Michael addition reaction as a key synthetic transformation. Special attention is paid to asymmetric methods featuring synthetically useful stereochemical outcomes and operational simplicity.

引用

页数：39

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