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

Uthoff, Florian; Gröger, Harald

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

Uthoff F, Gröger H (2018)
JOURNAL OF ORGANIC CHEMISTRY 83(16): 9517-9521.

Zeitschriftenaufsatz | Veröffentlicht | Englisch

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DOI

https://doi.org/10.1021/acs.joc.8b01247

Autor*in

Uthoff, Florian^UniBi; Gröger, Harald^UniBi

Einrichtung

Fakultät für Chemie > Industrielle Organische Chemie und Biotechnologie

Abstract / Bemerkung

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.

Erscheinungsjahr

2018

Zeitschriftentitel

JOURNAL OF ORGANIC CHEMISTRY

Band

Ausgabe

Seite(n)

9517-9521

ISSN

0022-3263

Page URI

https://pub.uni-bielefeld.de/record/2931113

Zitieren

Uthoff F, Gröger H. Asymmetric Synthesis of 1-Phenylethylamine from Styrene via Combined Wacker Oxidation and Enzymatic Reductive Amination. JOURNAL OF ORGANIC CHEMISTRY. 2018;83(16):9517-9521.

Uthoff, F., & Gröger, H. (2018). Asymmetric Synthesis of 1-Phenylethylamine from Styrene via Combined Wacker Oxidation and Enzymatic Reductive Amination. JOURNAL OF ORGANIC CHEMISTRY, 83(16), 9517-9521. doi:10.1021/acs.joc.8b01247

Uthoff, Florian, and Gröger, Harald. 2018. “Asymmetric Synthesis of 1-Phenylethylamine from Styrene via Combined Wacker Oxidation and Enzymatic Reductive Amination”. JOURNAL OF ORGANIC CHEMISTRY 83 (16): 9517-9521.

Uthoff, F., and Gröger, H. (2018). Asymmetric Synthesis of 1-Phenylethylamine from Styrene via Combined Wacker Oxidation and Enzymatic Reductive Amination. JOURNAL OF ORGANIC CHEMISTRY 83, 9517-9521.

Uthoff, F., & Gröger, H., 2018. Asymmetric Synthesis of 1-Phenylethylamine from Styrene via Combined Wacker Oxidation and Enzymatic Reductive Amination. JOURNAL OF ORGANIC CHEMISTRY, 83(16), p 9517-9521.

F. Uthoff and H. Gröger, “Asymmetric Synthesis of 1-Phenylethylamine from Styrene via Combined Wacker Oxidation and Enzymatic Reductive Amination”, JOURNAL OF ORGANIC CHEMISTRY, vol. 83, 2018, pp. 9517-9521.

Uthoff, F., Gröger, H.: Asymmetric Synthesis of 1-Phenylethylamine from Styrene via Combined Wacker Oxidation and Enzymatic Reductive Amination. JOURNAL OF ORGANIC CHEMISTRY. 83, 9517-9521 (2018).

Uthoff, Florian, and Gröger, Harald. “Asymmetric Synthesis of 1-Phenylethylamine from Styrene via Combined Wacker Oxidation and Enzymatic Reductive Amination”. JOURNAL OF ORGANIC CHEMISTRY 83.16 (2018): 9517-9521.