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Iridium Catalysed Asymmetric Hydrogenation of Pyridines
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Syntetisk organisk kemi.
2013 (engelsk)Licentiatavhandling, med artikler (Annet vitenskapelig)
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.

sted, utgiver, år, opplag, sider
Uppsala: Uppsala universitet, 2013. , s. 34
Emneord [en]
hydrogenation, pyridine, catalytic, Iridium
HSV kategori
Forskningsprogram
Organisk kemi
Identifikatorer
URN: urn:nbn:se:uu:diva-212413OAI: oai:DiVA.org:uu-212413DiVA, id: diva2:677724
Presentation
2013-05-31, Uppsala, 12:41 (engelsk)
Opponent
Veileder
Tilgjengelig fra: 2013-12-11 Laget: 2013-12-10 Sist oppdatert: 2017-01-25bibliografisk kontrollert
Delarbeid
1. Iridium-Catalyzed Asymmetric Hydrogenation of Substituted Pyridines
Åpne denne publikasjonen i ny fane eller vindu >>Iridium-Catalyzed Asymmetric Hydrogenation of Substituted Pyridines
2013 (engelsk)Inngår i: Asian Journal of Organic Chemistry, ISSN 2193-5807, Vol. 2, nr 12, s. 1061-1065Artikkel i tidsskrift (Fagfellevurdert) 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.

Emneord
hydrogenation, iridium, N-iminopyridium ylides, pyridines, selective catalysis
HSV kategori
Forskningsprogram
Organisk kemi
Identifikatorer
urn:nbn:se:uu:diva-212412 (URN)10.1002/ajoc.201300160 (DOI)000328218000008 ()
Tilgjengelig fra: 2013-12-10 Laget: 2013-12-10 Sist oppdatert: 2017-01-25bibliografisk kontrollert

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