Asymmetric Synthesis of 1-Phenylethylamine from Styrene via Combined Wacker Oxidation and Enzymatic Reductive Amination

被引：20

作者：

Uthoff, Florian ^{[1
]}

Groeger, Harald ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 16期

关键词：

AMINE DEHYDROGENASE; NONACTIVATED ALKENES; TERMINAL ALKENES; CHEMICAL-SHIFTS; SITE-ISOLATION; ALCOHOLS; KETONES; CATALYSIS; ALDEHYDES; SYSTEM;

D O I：

10.1021/acs.joc.8b01247

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective chemoenzymatic two-step one-pot transformation of styrene to 1-phenylethylamine has been developed based on combining an initial Pd/Cu-catalyzed Wacker oxidation of styrene with a subsequent reductive amination of the in situ formed acetophenone. As a nitrogen source only ammonia is needed. The incompatible catalysts were separated by means of a polydimethylsiloxane membrane, thus leading to quantitative conversion and an excellent enantiomeric excess of the corresponding amine. The overall one-pot process formally corresponds to an asymmetric hydroamination of styrene with ammonia.

引用

页码：9517 / 9521

页数：5