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Adaptative Biaryl Phosphite-Oxazole and Phosphite-Thiazole Ligands for Asymmetric Ir-Catalyzed Hydrogenation of Alkenes
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
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 15, 4567-4576 p.Article in journal (Refereed) Published
Abstract [en]

A library of readily available phosphite-oxazole/thiazole ligands (L1 a-g-L7 a-g) was applied in the Ir-catalyzed asymmetric hydrogenation of several largely unfunctionalized E- and Z-trisubstituted and 1,1-disubstituted terminal alkenes. The ability of the catalysts to transfer chiral information to the product could be tuned by choosing suitable ligand components (bridge length, the substituents in the heterocyclic ring and the alkyl backbone chain, the configuration of the ligand backbone, and the substituents/configurations in the biaryl phosphite moiety), so that enantioselectivities could be maximized for each substrate as required. Enantioselectivities were therefore excellent (enantiomeric excess (ee) values up to >99 %) for a wide range of E- and Z-trisubstituted and 1,1-disubstituted terminal alkenes. The biaryl phosphite moiety was a very advantageous ligand component in terms of substrate versatility.

Place, publisher, year, edition, pages
2010. Vol. 16, no 15, 4567-4576 p.
Keyword [en]
alkenes, asymmetric catalysis, hydrogenation, iridium, P, N ligands
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-121860DOI: 10.1002/chem.200903350ISI: 000277331000018PubMedID: 20229536OAI: oai:DiVA.org:uu-121860DiVA: diva2:306886
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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