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.

Download
Es wurde kein Volltext hochgeladen. Nur Publikationsnachweis!
Zeitschriftenaufsatz | Veröffentlicht | Englisch
Abstract / Bemerkung
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.
Erscheinungsjahr
Zeitschriftentitel
Angewandte Chemie (International ed. in English)
Band
54
Ausgabe
15
Seite(n)
4488-4492
ISSN
PUB-ID

Zitieren

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.

8 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Expanding the Spectrum of Light-Driven Peroxygenase Reactions.
Willot SJ, Fernández-Fueyo E, Tieves F, Pesic M, Alcalde M, Arends IWCE, Park CB, Hollmann F., ACS Catal 9(2), 2019
PMID: 30775065
From a Sequential to a Concurrent Reaction in Aqueous Medium: Ruthenium-Catalyzed Allylic Alcohol Isomerization and Asymmetric Bioreduction.
Ríos-Lombardía N, Vidal C, Liardo E, Morís F, García-Álvarez J, González-Sabín J., Angew Chem Int Ed Engl 55(30), 2016
PMID: 27258838
A One-Pot Cascade Reaction Combining an Encapsulated Decarboxylase with a Metathesis Catalyst for the Synthesis of Bio-Based Antioxidants.
Gómez Baraibar Á, Reichert D, Mügge C, Seger S, Gröger H, Kourist R., Angew Chem Int Ed Engl 55(47), 2016
PMID: 27754591
Chemoenzymatic one-pot synthesis in an aqueous medium: combination of metal-catalysed allylic alcohol isomerisation-asymmetric bioamination.
Ríos-Lombardía N, Vidal C, Cocina M, Morís F, García-Álvarez J, González-Sabín J., Chem Commun (Camb) 51(54), 2015
PMID: 26062926

53 References

Daten bereitgestellt von Europe PubMed Central.


AUTHOR UNKNOWN, 0

Clavier, Adv. Synth. Catal. 354(), 2012
Convergent strategies in biosynthesis.
Dairi T, Kuzuyama T, Nishiyama M, Fujii I., Nat Prod Rep 28(6), 2011
PMID: 21547300

AUTHOR UNKNOWN, 0

Denard, ACS Catal. 3(), 2013

Gröger, 2014

Makkee, J. Chem. Soc. Chem. Commun. (), 1980

Allen, Tetrahedron Lett. 37(), 1996

Larsson, Angew. Chem. Int. Ed. Engl. 36(), 1997

AUTHOR UNKNOWN, Angew. Chem. 109(), 1997
Aminocyclopentadienyl ruthenium chloride: catalytic racemization and dynamic kinetic resolution of alcohols at ambient temperature.
Choi JH, Kim YH, Nam SH, Shin ST, Kim MJ, Park J., Angew. Chem. Int. Ed. Engl. 41(13), 2002
PMID: 12203597

AUTHOR UNKNOWN, Angew. Chem. 114(), 2002
Lipase/aluminum-catalyzed dynamic kinetic resolution of secondary alcohols.
Berkessel A, Sebastian-Ibarz ML, Muller TN., Angew. Chem. Int. Ed. Engl. 45(39), 2006
PMID: 16952181

AUTHOR UNKNOWN, Angew. Chem. 118(), 2006
A chemoenzymatic approach to enantiomerically pure amines using dynamic kinetic resolution: application to the synthesis of norsertraline.
Thalen LK, Zhao D, Sortais JB, Paetzold J, Hoben C, Backvall JE., Chemistry 15(14), 2009
PMID: 19222068

Berkessel, ChemCatChem 3(), 2011
Synthetic cascades are enabled by combining biocatalysts with artificial metalloenzymes.
Kohler V, Wilson YM, Durrenberger M, Ghislieri D, Churakova E, Quinto T, Knorr L, Haussinger D, Hollmann F, Turner NJ, Ward TR., Nat Chem 5(2), 2012
PMID: 23344429

Simons, Top. Catal. 40(), 2006

Boffi, ChemCatChem 3(), 2011
Cooperative tandem catalysis by an organometallic complex and a metalloenzyme.
Denard CA, Huang H, Bartlett MJ, Lu L, Tan Y, Zhao H, Hartwig JF., Angew. Chem. Int. Ed. Engl. 53(2), 2014
PMID: 24536102

AUTHOR UNKNOWN, Angew. Chem. 126(), 2014

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, Angew. Chem. 120(), 2008
Sequential and modular synthesis of chiral 1,3-diols with two stereogenic centers: access to all four stereoisomers by combination of organo- and biocatalysis.
Baer K, Krausser M, Burda E, Hummel W, Berkessel A, Groger H., Angew. Chem. Int. Ed. Engl. 48(49), 2009
PMID: 19902444

AUTHOR UNKNOWN, Angew. Chem. 121(), 2009

Burda, ChemCatChem 2(), 2010

Tenbrink, Adv. Synth. Catal. 353(), 2011
Direction of kinetically versus thermodynamically controlled organocatalysis and its application in chemoenzymatic synthesis.
Rulli G, Duangdee N, Baer K, Hummel W, Berkessel A, Groger H., Angew. Chem. Int. Ed. Engl. 50(34), 2011
PMID: 21744441

AUTHOR UNKNOWN, Angew. Chem. 123(), 2011

Borchert, J. Mol. Catal. B 84(), 2012

Heidlindemann, ACS Catal. 4(), 2014

Hintermann, Top. Organomet. Chem. 31(), 2010

AUTHOR UNKNOWN, 0

McCarthy, Chem. Commun. (), 2000
Asymmetric enzymatic hydration of hydroxystyrene derivatives.
Wuensch C, Gross J, Steinkellner G, Gruber K, Glueck SM, Faber K., Angew. Chem. Int. Ed. Engl. 52(8), 2013
PMID: 23335002

AUTHOR UNKNOWN, Angew. Chem. 125(), 2013

AUTHOR UNKNOWN, 0
MhyADH catalysed Michael addition of water and in situ oxidation.
Jin J, Oskam PC, Karmee SK, Straathof AJ, Hanefeld U., Chem. Commun. (Camb.) 46(45), 2010
PMID: 20871891
The selective addition of water to C=C bonds; enzymes are the best chemists.
Jin J, Hanefeld U., Chem. Commun. (Camb.) 47(9), 2011
PMID: 21243161

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0
Cascade reactions using LiAlH4 and grignard reagents in the presence of water.
Runge MB, Mwangi MT, Miller AL 2nd, Perring M, Bowden NB., Angew. Chem. Int. Ed. Engl. 47(5), 2008
PMID: 18081114

AUTHOR UNKNOWN, Angew. Chem. 120(), 2008
A materials approach to site-isolation of Grubbs catalysts from incompatible solvents and m-chloroperoxybenzoic acid.
Mwangi MT, Runge MB, Hoak KM, Schulz MD, Bowden NB., Chemistry 14(22), 2008
PMID: 18563767

Miller, Adv. Mater. 20(), 2008
Site-isolation and recycling of PdCl(2) using PDMS thimbles.
Miller AL, Bowden NB., J. Org. Chem. 74(13), 2009
PMID: 19558181

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®

Quellen

PMID: 25704961
PubMed | Europe PMC

Suchen in

Google Scholar