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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 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.
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2010 (engelsk)Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, nr 2, s. 620-638Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2010. Vol. 16, nr 2, s. 620-638
Emneord [en]
Allylic substitution, Asymmetric catalysis, Ligand design, N.P ligands, Palladium
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Identifikatorer
URN: urn:nbn:se:uu:diva-121861DOI: 10.1002/chem.200901842ISI: 000274265100030PubMedID: 19937621OAI: oai:DiVA.org:uu-121861DiVA, id: diva2:306885
Tilgjengelig fra: 2010-03-31 Laget: 2010-03-31 Sist oppdatert: 2017-12-12bibliografisk kontrollert

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