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Enantiopure 1,5-diols from dynamic kinetic asymmetric transformation: Useful synthetic intermediates for the preparation of heterocycles
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.
Responsible organisation
2008 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 10, no 10, 2027-2030 p.Article in journal (Refereed) Published
Abstract [en]

Dynamic kinetic asymmetric transformation (DYKAT) of a series of 1,5-diols has been performed in the presence of Candida antarctica lipase B (CALB), Pseudomonas cepacia lipase H (PS-C II), and ruthenium catalyst 4. The resulting optically pure 1,5-diacetates are useful synthetic intermediates, which was demonstrated by the syntheses of both an enantiopure 2,6-disubstituted piperidine and an enantiopure 3,5-disubstituted morpholine.

Place, publisher, year, edition, pages
2008. Vol. 10, no 10, 2027-2030 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-25570DOI: 10.1021/ol800468hISI: 000255694100038OAI: oai:DiVA.org:su-25570DiVA: diva2:199993
Available from: 2008-11-06 Created: 2008-10-28 Last updated: 2012-06-26Bibliographically 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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