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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Integrated catalysis opens new arylation pathways via regiodivergent enzymatic C-H activation.
Latham J, Henry JM, Sharif HH, Menon BR, Shepherd SA, Greaney MF, Micklefield J., Nat Commun 7(), 2016
PMID: 27283121

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