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Iridium-catalyzed enantioselective hydrogenation of vinyl boronates
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi I.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi.
2009 (engelsk)Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, nr 40, s. 5996-5998Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

The first Ir-catalyzed asymmetric hydrogenations of vinyl boronates have been performed using low catalyst loadings (0.5 mol%) and pressure (as low as 1 bar). Good selectivities (76-98% ee) were obtained for a range of substrates.

sted, utgiver, år, opplag, sider
2009. nr 40, s. 5996-5998
HSV kategori
Identifikatorer
URN: urn:nbn:se:uu:diva-121862DOI: 10.1039/b912590fISI: 000270542300008PubMedID: 19809622OAI: oai:DiVA.org:uu-121862DiVA, id: diva2:306883
Tilgjengelig fra: 2010-03-31 Laget: 2010-03-31 Sist oppdatert: 2017-12-12bibliografisk kontrollert
Inngår i avhandling
1. Asymmetric Hydrogenations using N, P - Ligated Iridium Complexes
Åpne denne publikasjonen i ny fane eller vindu >>Asymmetric Hydrogenations using N, P - Ligated Iridium Complexes
2012 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

The research described in this thesis focuses on the catalytic asymmetric hydrogenation of prochiral olefins using N, P – chelated iridium catalysts. This catalytic system is tolerant to a wide range of substrates and performs better than the well-known ruthenium- and rhodium-catalytic systems for substrates devoid of coordinating groups in proximity of the olefin. Low catalytic loadings (often <1 %) and the high atom efficiency of this reaction make it a synthetically useful method of chiral molecule synthesis. The primary aim of this thesis was to develop new catalysts that rapidly and efficiently hydrogenate a broad range of alkenes asymmetrically. Papers I and II describe the synthesis and evaluation of new, highly efficient, chiral N, P – ligated iridium complexes. These catalysts were obtained in relatively few steps, while leaving open possibilities to modify and fine-tune their structure. Their versatility is ideally suited to both industrial uses and to equip any catalyst box. Paper III deals with a common problem of defluorination of vinylic fluorides during the hydrogenation. The catalyst designed in that work performs well for several substrates giving very low defluorination rates making it a good starting point for further improvements to cover a broader scope of vinyl fluorides. The structures of the catalysts from papers I and III also offers an easy approach to attach the catalyst ligands to a solid support. Paper IV explores hydrogenation of vinyl boronates, which gives synthetically interesting borane compounds with high enantioselectivities. Taking into account the rich chemistry of organic boranes, these compounds are very important. Paper V deals with hydrogenation of diphenylvinylphosphine oxides and vinyl phosphonates, another important classes of substrates that give chiral phosphorous containing compounds of interest in many fields of chemistry: such as medicinal chemistry and organocatalysis. In papers VI and VII we explore the Birch reaction as a source of prochiral olefins. By combining asymmetric hydrogenation with it, we obtain a powerful method to create chiral compounds with excellent enantioselectivities that are next to impossible to make by other routes. The products of the asymmetric hydrogenation are further modified by other well-known transformation to create other induced stereogenic centres.

sted, utgiver, år, opplag, sider
Uppsala: Acta Universitatis Upsaliensis, 2012. s. 61
Serie
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 939
Emneord
asymmetric hydrogenation, iridium, birch, boronates, fluorine
HSV kategori
Identifikatorer
urn:nbn:se:uu:diva-173459 (URN)978-91-554-8380-7 (ISBN)
Disputas
2012-06-08, B41, Husargatan 3, BMC, Uppsala, 10:15 (engelsk)
Opponent
Veileder
Tilgjengelig fra: 2012-05-15 Laget: 2012-04-24 Sist oppdatert: 2012-08-01bibliografisk kontrollert

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