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Olefin-Directed Palladium-Catalyzed Regio- and Stereoselective Oxidative Arylation of Allenes
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
2015 (Engelska)Ingår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 54, nr 31, s. 9066-9069Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

An olefin-directed palladium-catalyzed oxidative regio- and stereoselective arylation of allenes to afford 1,3,6-trienes has been established. A number of functionalized allenes, including 2,3- and 3,4-dienoates and 3,4-dienol derivatives, have been investigated and found to undergo the olefin-directed allene arylation. The olefin moiety has been proven to be a crucial element for the arylating transformation.

Ort, förlag, år, upplaga, sidor
2015. Vol. 54, nr 31, s. 9066-9069
Nyckelord [en]
allenes, arylation, directing groups, oxidation, palladium
Nationell ämneskategori
Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-120087DOI: 10.1002/anie.201502924ISI: 000358501500035OAI: oai:DiVA.org:su-120087DiVA, id: diva2:851657
Forskningsfinansiär
EU, Europeiska forskningsrådetVetenskapsrådetBerzelii Centre EXSELENTKnut och Alice Wallenbergs StiftelseTillgänglig från: 2015-09-07 Skapad: 2015-09-01 Senast uppdaterad: 2017-04-18Bibliografiskt granskad
Ingår i avhandling
1. Catalytic Stereoselective Formation of C–O, C–C and C–B Bonds: A Voyage from Asymmetric Reactions Enabled by Lipases to Stereoselective Palladium-Catalyzed Oxidative Transformations of Enallenes
Öppna denna publikation i ny flik eller fönster >>Catalytic Stereoselective Formation of C–O, C–C and C–B Bonds: A Voyage from Asymmetric Reactions Enabled by Lipases to Stereoselective Palladium-Catalyzed Oxidative Transformations of Enallenes
2017 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

This thesis has been focused on enzymatic kinetic resolutions and stereoselective oxidative transformations of enallenes catalyzed by PdII.

In the first part of the thesis, a detailed discussion on Candida antarctica lipase B (CALB)-catalyzed kinetic resolution (KR) of δ-functionalized alkan-2-acetates is shown. We gained a deeper insight into the mechanism of enzyme-substrate recognition. Changing from an anhydrous solvent to water or a water-containing organic solvent enhanced the enantioselectivity. The effect of –OH was also confirmed by a lipase mutant suggesting that the water molecule mentioned above can be partly mimicked.

In the second part of the thesis, we developed an efficient KR for allenic alcohols. On this basis, a novel synthesis of optically pure 2-substituted 2,3-dihydrofurans from allenic alcohols via a Ru-catalyzed cycloisomerization was reported. The developed protocol enabled us to assemble an optically pure precursor for total synthesis with three chiral centers from readily available allenol in 2 days.

In the third part, we reported a class of reactions involving C–H cleavage under mild conditions: PdII-catalyzed oxidative transformations of enallenes. These reactions are particularly attractive since a number of meticulous structures have been achieved from readily accessible starting materials. The directing effect of an unsaturated hydrocarbon was found to be key for these transformations.

In the final part, we developed the carbonylative insertion reaction discussed in the third part of the thesis into an asymmetric version. By using this methodology, a number of cyclopentenone compounds were obtained in good to excellent enantioselectivity.

Ort, förlag, år, upplaga, sidor
Stockholm: Department of Organic Chemistry, Stockholm University, 2017. s. 76
Nyckelord
Synthesis, Enzymatic kinetic resolution, Palladium, Allenes, Oxidative Transformations, Ruthenium
Nationell ämneskategori
Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-141519 (URN)978-91-7649-823-1 (ISBN)978-91-7649-824-8 (ISBN)
Disputation
2017-05-17, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 13:00 (Engelska)
Opponent
Handledare
Tillgänglig från: 2017-04-24 Skapad: 2017-04-05 Senast uppdaterad: 2017-05-23Bibliografiskt granskad

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Av författaren/redaktören
Zhu, CanYang, BinJiang, TuoBäckvall, Jan-E.
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Institutionen för organisk kemi
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Angewandte Chemie International Edition
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