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

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

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...

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Veröffentlicht in:Journal of organic chemistry 2018-08, Vol.83 (16), p.9517-9521
Hauptverfasser: Uthoff, Florian, Gröger, Harald
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Gröger, Harald
description 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.
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title Asymmetric Synthesis of 1‑Phenylethylamine from Styrene via Combined Wacker Oxidation and Enzymatic Reductive Amination
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