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Enzymatic resolution, desymmetrization and dynamic kinetic asymmetric transformation of 1,3-cycloalkanediols
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Responsible organisation
2006 In: Journal of organic chemistry, ISSN 0022-3263, Vol. 71, no 17, 6309-6316 p.Article in journal (Refereed) Published
Place, publisher, year, edition, pages
2006. Vol. 71, no 17, 6309-6316 p.
Identifiers
URN: urn:nbn:se:su:diva-25573OAI: oai:DiVA.org:su-25573DiVA: diva2:199996
Note
Part of urn:nbn:se:su:diva-8294Available from: 2008-11-06 Created: 2008-10-28Bibliographically approved
In thesis
1. Synthesis and asymmetric transformations of diols by enzyme- and ruthenium catalysis
Open this publication in new window or tab >>Synthesis and asymmetric transformations of diols by enzyme- and ruthenium catalysis
2008 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The major part of this thesis describes the synthesis of aliphatic secondary diols and the development of lipase- and ruthenium-catalyzed asymmetric transformations of these diols.

Several acyclic 1,4-diols and 1,5-diols were synthesized, and by combining a lipase-catalyzed asymmetric transformation with a ruthenium-catalyzed epimerization, enantiomerically- and diastereomerically enriched diacetates were obtained. The scope and limitations of the system were also investigated, and some problems were encountered with electron-deficient diols. The diacetate products were further transformed into natural product heterocycles and chiral ligands.

A thorough study of the enzyme-catalyzed asymmetric transformation of 1,3-cyclohexanediol was also performed. It was found that there was a difference in the enzyme selectivity for the cis- and trans- diols, respectively, and while poor selectivity was observed for the trans-diol, cis-1,3-cyclohexanediol could be efficiently desymmetrized. By adding different epimerization catalysts, both cis- and trans-1,3-cyclohexanediol could be obtained in high enantio- and diastereoselectivities.

The use of hydrogen transfer for the reduction of cyclic 1,3-diketones was also demonstrated, and the reactions could in many cases be carried out in a microwave oven.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi, 2008. 49 p.
Keyword
dynamic kinetic asymmetric transformation, diols, enzymatic transformations, catalysis, ruthenium, transfer hydrogenation
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-8294 (URN)978-91-7155-769-8 (ISBN)
Public defence
2008-11-28, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 14:00
Opponent
Supervisors
Available from: 2008-11-06 Created: 2008-10-28 Last updated: 2011-02-28Bibliographically approved

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