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Highly Efficient Redox Isomerization of Allylic Alcohols at Ambient Temperature Catalyzed by Novel Ruthenium-Cyclopentadienyl Complexes–Insight into the Racemization Mechanism
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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2005 In: Chemistry : a European journal, ISSN 0947-6539, Vol. 11, no 20, 5832-5842 p.Article in journal (Refereed) Published
Place, publisher, year, edition, pages
2005. Vol. 11, no 20, 5832-5842 p.
Identifiers
URN: urn:nbn:se:su:diva-24333OAI: oai:DiVA.org:su-24333DiVA: diva2:197248
Note
Part of urn:nbn:se:su:diva-6876Available from: 2007-05-30 Created: 2007-05-23Bibliographically 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
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Available from: 2007-05-30 Created: 2007-05-23 Last updated: 2017-10-16Bibliographically approved

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