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High-yielding metalloenzymatic dynamic kinetic resolution of fluorinated aryl alcohols
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2007 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1873-3581, Vol. 48, no 31, 5471-5474 p.Article in journal (Refereed) Published
Abstract [en]

Dynamic kinetic resolution (DKR) of various fluorinated aryl alcohols by a combination of lipase-catalyzed enzymatic resolution with in situ ruthenium-catalyzed alcohol racemization is described. (R)-Selective Candida antarctica lipase B (CALB) was employed for transesterification of different fluoroaryl alcohols in DKR reactions delivering the corresponding acetates in high yield (97%) with excellent enantiomeric excess (98%).

Place, publisher, year, edition, pages
2007. Vol. 48, no 31, 5471-5474 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-24336DOI: 10.1016/j.tetlet.2007.05.175ISI: 000248527400026OAI: oai:DiVA.org:su-24336DiVA: diva2:197251
Available from: 2007-05-30 Created: 2007-05-23 Last updated: 2011-05-23Bibliographically approved
In thesis
1. Synthetic Transformations via Metal- and Enzyme-Catalyzed Dynamic Kinetic Resolution
Open this publication in new window or tab >>Synthetic Transformations via Metal- and Enzyme-Catalyzed Dynamic Kinetic Resolution
2007 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis deals with the preparation of a new half-sandwich type ruthenium(II)- catalyst for racemization of optically active secondary alcohols and the development of a highly efficient method in combination with lipases such as Candida antarctica lipase B and Pseudomonas cepacia lipase for dynamic kinetic resolution of various functionalized alcohols under mild reaction conditions.

It was shown that the RuCl(CO)25-C5Ph5) complex can racemize optically active aliphatic and aromatic secondary alcohols at room temperature in rather short times. Different parameters, such as the nature of the catalyst, catalyst loading and solvent effect were studied. After the optimization steps, the Ru-catalyzed racemization of (S)-1-phenylethanol in the presence of Candida antarctica lipase B was also investigated. The compatibility of the metal- and enzyme-catalyzed reactions led to a highly efficient coupled catalytic system for transformation of racemic alcohols to their enantiomerically pure acetates. This protocol was applied for a wide range of secondary alcohols. It was shown that in the case of allylic alcohols the obtained enantiopure allylic acetates are useful compounds for synthesis of α-methyl carboxylic acids such as (R)-Flurbiprofen and acyloin acetates. Highly selective dynamic kinetic asymmetric transformation of 3,5-piperidine diol to deliver various 3,5-dioxygenated piperidines is also described.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi, 2007. 66 p.
Keyword
ruthenium, racemization, lipase, dynamic kinetic resolution, secondary alcohol, Candida antarctica lipase B
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-6876 (URN)978-91-7155-463-5 (ISBN)
Public defence
2007-06-20, Magnélisalen, Arrheniuslaboratoriet, Svante Arrhenius väg 12, Stockholm, 10:00
Opponent
Supervisors
Available from: 2007-05-30 Created: 2007-05-23 Last updated: 2017-10-16Bibliographically approved

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