Cooperative Catalysis of Noncompatible Catalysts through Compartmentalization: Wacker Oxidation and Enzymatic Reduction in a One-Pot Process in Aqueous Media

Sato H, Hummel W, Gröger H (2015)
Angewandte Chemie (International ed. in English) 54(15): 4488-4492.

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Abstract
A Wacker oxidation using CuCl/PdCl2 as a catalyst system was successfully combined with an enzymatic ketone reduction to convert styrene enantioselectively into 1-phenylethanol in a one-pot process, although the two reactions conducted in aqueous media are not compatible due to enzyme deactivation by Cu ions. The one-pot feasibility was achieved via compartmentalization of the reactions. Conducting the Wacker oxidation in the interior of a polydimethylsiloxane thimble enables diffusion of only the organic substrate and product into the exterior where the biotransformation takes place. Thus, the Cu ions detrimental to the enzyme are withheld from the reaction media of the biotransformation. In this one-pot process, which formally corresponds to an asymmetric hydration of alkenes, a range of 1-arylethanols were formed with high conversions and 98-99 % ee. In addition, the catalyst system of the Wacker oxidation was recycled 15 times without significant decrease in conversion.
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Sato H, Hummel W, Gröger H. Cooperative Catalysis of Noncompatible Catalysts through Compartmentalization: Wacker Oxidation and Enzymatic Reduction in a One-Pot Process in Aqueous Media. Angewandte Chemie (International ed. in English). 2015;54(15):4488-4492.
Sato, H., Hummel, W., & Gröger, H. (2015). Cooperative Catalysis of Noncompatible Catalysts through Compartmentalization: Wacker Oxidation and Enzymatic Reduction in a One-Pot Process in Aqueous Media. Angewandte Chemie (International ed. in English), 54(15), 4488-4492. doi:10.1002/anie.201409590
Sato, H., Hummel, W., and Gröger, H. (2015). Cooperative Catalysis of Noncompatible Catalysts through Compartmentalization: Wacker Oxidation and Enzymatic Reduction in a One-Pot Process in Aqueous Media. Angewandte Chemie (International ed. in English) 54, 4488-4492.
Sato, H., Hummel, W., & Gröger, H., 2015. Cooperative Catalysis of Noncompatible Catalysts through Compartmentalization: Wacker Oxidation and Enzymatic Reduction in a One-Pot Process in Aqueous Media. Angewandte Chemie (International ed. in English), 54(15), p 4488-4492.
H. Sato, W. Hummel, and H. Gröger, “Cooperative Catalysis of Noncompatible Catalysts through Compartmentalization: Wacker Oxidation and Enzymatic Reduction in a One-Pot Process in Aqueous Media”, Angewandte Chemie (International ed. in English), vol. 54, 2015, pp. 4488-4492.
Sato, H., Hummel, W., Gröger, H.: Cooperative Catalysis of Noncompatible Catalysts through Compartmentalization: Wacker Oxidation and Enzymatic Reduction in a One-Pot Process in Aqueous Media. Angewandte Chemie (International ed. in English). 54, 4488-4492 (2015).
Sato, Hirofumi, Hummel, Werner, and Gröger, Harald. “Cooperative Catalysis of Noncompatible Catalysts through Compartmentalization: Wacker Oxidation and Enzymatic Reduction in a One-Pot Process in Aqueous Media”. Angewandte Chemie (International ed. in English) 54.15 (2015): 4488-4492.
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A One-Pot Cascade Reaction Combining an Encapsulated Decarboxylase with a Metathesis Catalyst for the Synthesis of Bio-Based Antioxidants.
Gomez Baraibar A, Reichert D, Mugge C, Seger S, Groger H, Kourist R., Angew. Chem. Int. Ed. Engl. 55(47), 2016
PMID: 27754591
From a Sequential to a Concurrent Reaction in Aqueous Medium: Ruthenium-Catalyzed Allylic Alcohol Isomerization and Asymmetric Bioreduction.
Rios-Lombardia N, Vidal C, Liardo E, Moris F, Garcia-Alvarez J, Gonzalez-Sabin J., Angew. Chem. Int. Ed. Engl. 55(30), 2016
PMID: 27258838
Chemoenzymatic one-pot synthesis in an aqueous medium: combination of metal-catalysed allylic alcohol isomerisation-asymmetric bioamination.
Rios-Lombardia N, Vidal C, Cocina M, Moris F, Garcia-Alvarez J, Gonzalez-Sabin J., Chem. Commun. (Camb.) 51(54), 2015
PMID: 26062926

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