Enantioselective One-Pot Synthesis of Biaryl-Substituted Amines by Combining Palladium and Enzyme Catalysis in Deep Eutectic Solvents

被引：47

作者：

Paris, Juraj ^{[1
,2
]}

Telzerow, Aline ^{[3
,4
]}

Rios-Lombardia, Nicolas ^{[1
]}

Steiner, Kerstin ^{[3
]}

Schwab, Helmut ^{[3
]}

Moris, Francisco ^{[1
]}

Groeger, Harald ^{[2
]}

Gonzalez-Sabin, Javier ^{[1
]}

机构：

[1] EntreChem SL, Vivero Ciencias Salud, Oviedo 33011, Spain

[2] Bielefeld Univ, Fac Chem, Chair Organ Chem 1, Univ Str 25, D-33615 Bielefeld, Germany

[3] Graz Univ Technol, Inst Mol Biotechnol, Petersgasse 14, A-8010 Graz, Austria

[4] InnoSyn BV, Urmonderbaan 22, NL-6167RD Geleen, Netherlands

来源：

ACS SUSTAINABLE CHEMISTRY & ENGINEERING | 2019年 / 7卷 / 05期

基金：

欧盟地平线“2020”;

关键词：

Amines; Asymmetric synthesis; Biocatalysis; Deep eutectic solvents; Palladium catalysis; Suzuki cross-coupling reaction; ASYMMETRIC-SYNTHESIS; ROOM-TEMPERATURE; BIOCATALYSIS; COMBINATION; CYCLOISOMERIZATION; BIOTRANSFORMATIONS; MIXTURES; ALCOHOLS; MEDIA; WATER;

D O I：

10.1021/acssuschemeng.8b06715

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first application of Deep Eutectic Solvents (DESs) in asymmetric bioamination of ketones has been accomplished. The amine transaminases (ATAs) turned out to be particularly stable in DES-buffer mixtures at a percentage of up to 75% (w/w) neoteric solvent. Moreover, this reaction medium was used to perform a chemoenzymatic cascade toward biaryl amines by coupling a Suzuki reaction sequentially with an enantioselective bioamination catalyzed by the recently discovered ATA from Exophiala xenobiotica (EX-wTA). The solubilizing properties of DESs enabled the metal catalyzed step at 200 mM loading of substrate and the subsequent biotransformation at 25 mM.

引用

页码：5486 / 5493

页数：15

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