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A new class of modular P,N-ligand library for asymmetric Pd-catalyzed allylic substitution reactions: a study of the key Pd-pi-allyl intermediates
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
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2010 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, no 2, 620-638 p.Article in journal (Refereed) Published
Abstract [en]

A new class of modular P,N-ligand library has been synthesized and screened in the Pd-catalyzed allylic substitution reactions of several substrate types. These series of ligands can be prepared efficiently from easily accessible hydroxyl-oxazole/thiazole derivatives. Their modular nature enables the bridge length, the substituents at the heterocyclic ring and in the alkyl backbone chain, the configuration of the ligand backbone, and the substituents/configurations in the biaryl phosphite moiety to be easily and systematically varied. By carefully selecting the ligand components, therefore, high regio- and enantioselectivities (ee values up to 96 %) and good activities are achieved in a broad range of mono-, di-, and trisubstituted linear hindered and unhindered substrates and cyclic substrates. The NMR spectroscopic and DFT studies on the Pd-pi-allyl intermediates provide a deeper understanding of the effect of ligand parameters on the origin of enantioselectivity.

Place, publisher, year, edition, pages
2010. Vol. 16, no 2, 620-638 p.
Keyword [en]
Allylic substitution, Asymmetric catalysis, Ligand design, N.P ligands, Palladium
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-121861DOI: 10.1002/chem.200901842ISI: 000274265100030PubMedID: 19937621OAI: oai:DiVA.org:uu-121861DiVA: diva2:306885
Available from: 2010-03-31 Created: 2010-03-31 Last updated: 2017-12-12Bibliographically approved

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Andersson, Pher G

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