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Chemoenzymatic Dynamic Kinetic Resolution of Secondary Alcohols Using an Air- and Moisture-Stable Iron Racemization Catalyst
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Number of Authors: 42017 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 23, no 5, p. 1048-1051Article in journal (Refereed) Published
Abstract [en]

Herein, we report on a metalloenzymatic dynamic kinetic resolution of sec-alcohols employing an iron-based racemization catalyst together with a lipase. The iron catalyst was evaluated in racemization and then used in dynamic kinetic resolution of a number of sec-alcohols to give enantiomerically pure products in good to high yields. The iron catalyst is air and moisture stable and is readily accessible.

Place, publisher, year, edition, pages
2017. Vol. 23, no 5, p. 1048-1051
Keywords [en]
dynamic kinetic resolution, enzyme catalysis, iron catalysis, racemization, secondary alcohols
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-141286DOI: 10.1002/chem.201605754ISI: 000395753000014PubMedID: 28005307OAI: oai:DiVA.org:su-141286DiVA, id: diva2:1086882
Available from: 2017-04-04 Created: 2017-04-04 Last updated: 2018-03-09Bibliographically approved
In thesis
1. Studies on Metalloenzymatic Dynamic Kinetic Resolutions and Iron-Catalyzed Reactions of Allenes
Open this publication in new window or tab >>Studies on Metalloenzymatic Dynamic Kinetic Resolutions and Iron-Catalyzed Reactions of Allenes
2018 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The main focus of this thesis lies in the development of new transition metal-catalyzed chemoenzymatic dynamic kinetic resolutions (DKR) of both alcohols and amines. The first part of the thesis deals with the development of new heterogeneous systems for the DKR of amines. The racemization catalysts in these different systems are all composed of palladium nanoparticles supported on either mesoporous silica or incorporated in a biocomposite that is composed of a bioactive cross-linked enzyme aggregate. 

The second part of the thesis deals with the development of a homogeneous iron catalyst in the racemization of sec-alcohols for the implementation in a chemoenzymatic DKR. Two protocols for the racemization of sec-alcohols are reported. The first one could not be combined with a chemoenzymatic kinetic resolution, although this was overcome in the second iron based protocol. 

Following the successful iron catalyzed chemoenzymatic DKR of sec-alcohols, the iron catalyst was used in the cyclization of α-allenic alcohols and N-protected amines to furnish 2,3-dihydrofurans and 2,3-dihydropyrroles, respectively. The cyclization is proceeding in a diastereoselective manner.

The last part of the thesis deals with attempts to further elucidate the mechanism of activation of a known ruthenium racemization catalyst. X-ray absorption spectroscopy using synchrotron radiation was used for this purpose.

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2018. p. 97
Keywords
Racemization, Dynamic Kinetic Resolution, Enzyme Catalysis, XAS, Asymmetric Synthesis
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-153952 (URN)978-91-7797-195-5 (ISBN)978-91-7797-196-2 (ISBN)
Public defence
2018-04-27, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (English)
Opponent
Supervisors
Note

At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 4: Manuscript. Paper 7: Manuscript. Paper 8: Manuscript.

Available from: 2018-04-04 Created: 2018-03-09 Last updated: 2018-03-22Bibliographically approved

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