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Development of pinene-derived N,P ligands and their utility in catalytic asymmetric hydrogenation
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
2007 (English)In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, no 47, 5603-5610 p.Article in journal (Refereed) Published
Abstract [en]

New diastereomeric N,P-ligands, derived from the natural product (+)--pinene, have been synthesized and evaluated in iridium-catalyzed asymmetric hydrogenation. The ligands are tetrahydroquinoline derivatives synthesized directly from commercially available -pinene utilizing resolution or recrystallization to separate diastereomers. In reduction of a range of different trisubstituted alkenes the catalysts express very different activities ranging from no activity to high activity. One of the catalysts gives good ee values for some substrates.

Place, publisher, year, edition, pages
2007. no 47, 5603-5610 p.
National Category
Chemical Sciences
URN: urn:nbn:se:uu:diva-12344DOI: 10.1039/b713257nISI: 000251269100016OAI: oai:DiVA.org:uu-12344DiVA: diva2:40113
Available from: 2007-12-13 Created: 2007-12-13 Last updated: 2012-11-12Bibliographically approved
In thesis
1. Transition Metal Catalysis for Selective Synthesis and Sustainable Chemistry
Open this publication in new window or tab >>Transition Metal Catalysis for Selective Synthesis and Sustainable Chemistry
2012 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis discusses the preparation and use of transition-metal catalysts for selective organic chemical reactions. Specifically, two different matters have been studied; the asymmetric hydrogenation of carbon-carbon double bonds using N,P-ligated iridium catalysts and the metal-catalyzed transfer of small molecules from biomass to synthetic intermediates.

In the first part of this thesis, chiral N,P-ligands were synthesized and evaluated in iridium catalysts for the asymmetric hydrogenation of non- and weakly functionalized alkenes (Papers I & II). The new catalysts were prepared via chiral-pool strategies and exhibited superior properties for the reduction of certain types of alkenes. In particular, some of the catalysts showed excellent activity and selectivity in the enantioselective reduction of terminal alkenes, and the preparation of a modular catalyst library allowed the asymmetric hydrogenation of a wide range of 1,1-disubstituted alkenes with unprecedented efficiency and enantioselectivity (Paper III). Methods for the selective preparation of chiral hetero- and carbocyclic fragments using iridium-catalyzed asymmetric hydrogenation as an enantiodetermining key step were also developed. A range of elusive chiral building blocks that have applications in pharmaceutical and natural-product chemistry could thus be conveniently prepared (Papers IV & V).

The second part of this thesis deals with the catalytic decomposition of polysaccharides into sugar alcohols and the incorporation of their decomposition products into alkene substrates. Iridium-catalyzed dehydrogenative decarbonylation was found to decompose polyols into CO:H2 mixtures that could be used immediately in the ex situ low-pressure hydroformylation of styrene (Paper VI). The net process was thus the hydroformylation of alkenes with biomass-derived synthesis gas.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2012. 125 p.
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 984
Catalysis, Transition metals, Asymmetric catalysis, Hydrogenation, Sustainable chemistry
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
urn:nbn:se:uu:diva-182900 (URN)978-91-554-8507-8 (ISBN)
Public defence
2012-11-30, B42, BMC, Husargatan 3, Uppsala, 10:00 (English)
Available from: 2012-11-09 Created: 2012-10-18 Last updated: 2013-01-23

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Verendel, JohanAndersson, Pher G.
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