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Thiazole, Imidazole and Oxazoline Based N,P-Ligands for Palladium-Catalyzed Cycloisomerization of 1,6-Enynes
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.ORCID-id: 0000-0002-6053-8828
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Vise andre og tillknytning
2016 (engelsk)Inngår i: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, nr 20, s. 3427-3433Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

A series of N,P-ligands were prepared and evaluated in the asymmetric palladium-catalyzed cycloisomerization of allyl propargyl ether substrates. The reactivity and enantioselectivity of the reaction was shown to be highly dependent on the chiral skeleton of the ligand structures with ee's ranging from 22-99 %. The proton source had a significant impact on the enantioselectivity. The generation of palladium hydride from formic acid led to the highest ee. A selectivity model based on a proposed transition state was used to predict and explain the enantiomeric outcome of the reaction.

sted, utgiver, år, opplag, sider
Wiley-VCH Verlagsgesellschaft, 2016. nr 20, s. 3427-3433
Emneord [en]
Cyclization, Isomerization, Enynes, N, P ligands, Palladium, Density functional calculations
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-133232DOI: 10.1002/ejoc.201600468ISI: 000380138100023OAI: oai:DiVA.org:su-133232DiVA, id: diva2:968442
Forskningsfinansiär
Swedish Research CouncilStiftelsen Olle Engkvist ByggmästareSwedish Energy AgencyKnut and Alice Wallenberg FoundationVinnovaTilgjengelig fra: 2016-09-12 Laget: 2016-09-05 Sist oppdatert: 2019-07-17bibliografisk kontrollert
Inngår i avhandling
1. The Use of N,P-Iridium and N,P-Palladium Complexes in Asymmetric Synthesis
Åpne denne publikasjonen i ny fane eller vindu >>The Use of N,P-Iridium and N,P-Palladium Complexes in Asymmetric Synthesis
2018 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

The work presented in this thesis concerns asymmetric catalysis using chiral N,P-ligands and iridium or palladium transition metals. The first part  (Chapters 2 and 3) highlights the N,P-iridium catalyzed asymmetric hydrogenation of 1,4-cyclohexadienes having functionalized or unfunctionalized substituents, including allylsilane side chains. A series of N,P-iridium catalysts were synthesized and screened on a number of cyclohexadienes. The developed N,P-iridium catalysts have provided excellent chemo-, regio- and enantioselectivity for most of the products obtained. For substrates having an allylsilane sidechain, the chiral cyclic allylsilane products were used to induce stereocontrol in a subsequent Hosomi-Sakurai reaction using TiCl4 as Lewis acid and aldehydes as electrophiles. The corresponding homoallylic alcohols were obtained in good to excellent diastereoselectivity. 

The second part (Chapter 4) describes the N,P-iridium catalyzed asymmetric hydrogenation of various vinyl fluorides. A number of tri- and tetrasubstituted vinyl fluorides were synthesized and evaluated for the asymmetric hydrogenation. The corresponding saturated chiral fluoro compounds were obtained in very high enantioselectivity (up to 99% ee). The defluorination, usually known to occur under the catalytic hydrogenation conditions, were not observed for the majority of the substrates. 

Finally, Chapter 5 describes the application of N,P-ligands in the asymmetric cycloisomerization of 1,6-enynes using a palladium precatalyst. The enantioselectivities for the products were found to depend both on the substrate as well as the hydrogen source. These developed catalytic reactions provide attractive methods to create multiple stereogenic centers in a molecule in relatively few steps from readily available starting materials.

sted, utgiver, år, opplag, sider
Stockholm: Department of Organic Chemistry, Stockholm University, 2018. s. 66
Emneord
Iridium, Asymmetric Hydrogenation, Palladium, Asymmetric Cycloisomerization and Hosomi-Sakurai Allylation
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-150602 (URN)978-91-7797-061-3 (ISBN)978-91-7797-062-0 (ISBN)
Disputas
2018-01-31, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (engelsk)
Opponent
Veileder
Merknad

At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 3: Manuscript.

Tilgjengelig fra: 2018-01-08 Laget: 2017-12-27 Sist oppdatert: 2018-01-11bibliografisk kontrollert

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