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Iridium Catalysed Asymmetric Hydrogenation of Pyridines
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
2013 (English)Licentiate thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis presents the hydrogenation of substituted pyridines using N,P-ligated iridium catalystsin homogeneous media. These iridium catalysts were developed within this research group in thepast decade. This method of hydrogenation is highly stereoselective, and in several cases good to excellent ees were obtained.The hydrogenation of substituted pyridines was studied: by screening for the catalyst giving thehighest conversion and ee, by optimising the reaction conditions and by attempting to improve existingcatalysts. New substrates were synthesised for this process, in particular alkyl substituted Nprotectedpyridines. Their reduction provided chiral piperidines, which could be used as chiralbuilding blocks once deprotected.

Place, publisher, year, edition, pages
Uppsala: Uppsala universitet, 2013. , 34 p.
Keyword [en]
hydrogenation, pyridine, catalytic, Iridium
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-212413OAI: oai:DiVA.org:uu-212413DiVA: diva2:677724
Presentation
2013-05-31, Uppsala, 12:41 (English)
Opponent
Supervisors
Available from: 2013-12-11 Created: 2013-12-10 Last updated: 2017-01-25Bibliographically approved
List of papers
1. Iridium-Catalyzed Asymmetric Hydrogenation of Substituted Pyridines
Open this publication in new window or tab >>Iridium-Catalyzed Asymmetric Hydrogenation of Substituted Pyridines
2013 (English)In: Asian Journal of Organic Chemistry, ISSN 2193-5807, Vol. 2, no 12, 1061-1065 p.Article in journal (Refereed) Published
Abstract [en]

Asymmetric hydrogenation of ortho-substituted pyridines catalyzed by N,P-ligated iridium is demonstrated. To facilitate this reaction, the aromaticity of the pyridines was weakened by forming N-iminopyridium ylides. The reactions give very high conversions, and after a single recrystallization, excellent ee of up to 98 % was obtained. This method lends itself to the synthesis of chiral piperidine building blocks.

Keyword
hydrogenation, iridium, N-iminopyridium ylides, pyridines, selective catalysis
National Category
Organic Chemistry Inorganic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-212412 (URN)10.1002/ajoc.201300160 (DOI)000328218000008 ()
Available from: 2013-12-10 Created: 2013-12-10 Last updated: 2017-01-25Bibliographically approved

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Citation style
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