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Asymmetric hydrogenation of α,β-unsaturated nitriles with base-activated iridium N,P ligand complexes

Müller, Marc-André and Pfaltz, Andreas. (2014) Asymmetric hydrogenation of α,β-unsaturated nitriles with base-activated iridium N,P ligand complexes. Angewandte Chemie International Edition, 53 (33). pp. 8668-8671.

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Official URL: http://edoc.unibas.ch/dok/A6337606

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Abstract

Although many chiral catalysts are known that allow highly enantioselective hydrogenation of a wide range of olefins, no suitable catalysts for the asymmetric hydrogenation of α,β-unsaturated nitriles have been reported so far. We have found that Ir N,P ligand complexes, which under normal conditions do not show any reactivity towards α,β-unsaturated nitriles, become highly active catalysts upon addition of N,N-diisopropylethylamine. The base-activated catalysts enable conjugate reduction of α,β-unsaturated nitriles with H2 at low catalyst loadings, affording the corresponding saturated nitriles with high conversion and excellent enantioselectivity. In contrast, alkenes lacking a conjugated cyano group do not react under these conditions, making it possible to selectively reduce the conjugated C=C bond of an α,β-unsaturated nitrile, while leaving other types of C=C bonds in the molecule intact.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische organische Chemie (Pfaltz)
UniBasel Contributors:Pfaltz, Andreas
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Wiley
ISSN:1433-7851
e-ISSN:1521-3773
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:10 Apr 2017 08:42
Deposited On:06 Feb 2015 09:59

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