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Thiazole, Imidazole and Oxazoline Based N,P-Ligands for Palladium-Catalyzed Cycloisomerization of 1,6-Enynes
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry. Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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Number of Authors: 6
2016 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 20, 3427-3433 p.Article in journal (Refereed) 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.

Place, publisher, year, edition, pages
2016. no 20, 3427-3433 p.
Keyword [en]
Cyclization, Isomerization, Enynes, N, P ligands, Palladium, Density functional calculations
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-133232DOI: 10.1002/ejoc.201600468ISI: 000380138100023OAI: oai:DiVA.org:su-133232DiVA: diva2:968442
Available from: 2016-09-12 Created: 2016-09-05 Last updated: 2016-09-12Bibliographically approved

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Quan, XuLiu, JianguoRabten, WangchukAndersson, Pher G.
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