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NeoPHOX - a structurally tunable ligand system for asymmetric catalysis

Padevět, Jaroslav and Schrems, Marcus G. and Scheil, Robin and Pfaltz, Andreas. (2016) NeoPHOX - a structurally tunable ligand system for asymmetric catalysis. Beilstein Journal of Organic Chemistry, 12. pp. 1185-1195.

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Abstract

A synthesis of new NeoPHOX ligands derived from serine or threonine has been developed. The central intermediate is a NeoPHOX derivative bearing a methoxycarbonyl group at the stereogenic center next to the oxazoline N atom. The addition of methylmagnesium chloride leads to a tertiary alcohol, which can be acylated or silylated to produce NeoPHOX ligands with different sterical demand. The new NeoPHOX ligands were tested in the iridium-catalyzed asymmetric hydrogenation and palladium-catalyzed allylic substitution. In both reactions high enantioselectivities were achieved, that were comparable to the enantioselectivities obtained with the up to now best NeoPHOX ligand derived from expensive tert-leucine.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische organische Chemie (Pfaltz)
UniBasel Contributors:Pfaltz, Andreas and Scheil, Robin
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Beilstein-Institut
e-ISSN:1860-5397
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
Identification Number:
Last Modified:25 Jan 2017 09:09
Deposited On:25 Jan 2017 09:09

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