Assisted Tandem Catalysis: Metathesis Followed by Asymmetric Hydrogenation from a Single Ruthenium Source

Here we report the first example of a tandem metathesis–asymmetric hydrogenation protocol where the prochiral olefin generated by metathesis is hydrogenated with high enantioselectivity by an in situ formed chiral ruthenium catalyst. We show that either the ruthenium metathesis catalysts or the ruth...

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Published in:	Advanced synthesis & catalysis Vol. 357; no. 10; pp. 2223 - 2228
Main Authors:	Renom-Carrasco, Marc, Gajewski, Piotr, Pignataro, Luca, de Vries, Johannes G., Piarulli, Umberto, Gennari, Cesare, Lefort, Laurent
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 06.07.2015 WILEY‐VCH Verlag Wiley
Subjects:	asymmetric catalysis Asymmetry Catalysis Catalysts Chemistry Chemistry, Applied Chemistry, Organic Decomposition reactions Hydrogenation Ligands Metathesis Physical Sciences Ruthenium Science & Technology tandem catalysis COMPLEXES DECOMPOSITION OLEFIN METATHESIS asymmetric catalysis hydrogenation TETRASUBSTITUTED OLEFINS SOLVENT ruthenium metathesis RING-CLOSING METATHESIS tandem catalysis LIGAND TRANSFORMATIONS
ISSN:	1615-4150, 1615-4169
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Abstract	Here we report the first example of a tandem metathesis–asymmetric hydrogenation protocol where the prochiral olefin generated by metathesis is hydrogenated with high enantioselectivity by an in situ formed chiral ruthenium catalyst. We show that either the ruthenium metathesis catalysts or the ruthenium species formed during the metathesis reaction can be converted into an efficient asymmetric hydrogenation catalyst upon addition of a chiral ligand and an alcohol. The performance in asymmetric hydrogenation appears to be very dependent on the solvent, the chiral ligand, and the prochiral substrate.
AbstractList	Here we report the first example of a tandem metathesis–asymmetric hydrogenation protocol where the prochiral olefin generated by metathesis is hydrogenated with high enantioselectivity by an in situ formed chiral ruthenium catalyst. We show that either the ruthenium metathesis catalysts or the ruthenium species formed during the metathesis reaction can be converted into an efficient asymmetric hydrogenation catalyst upon addition of a chiral ligand and an alcohol. The performance in asymmetric hydrogenation appears to be very dependent on the solvent, the chiral ligand, and the prochiral substrate. magnified image Here we report the first example of a tandem metathesis-asymmetric hydrogenation protocol where the prochiral olefin generated by metathesis is hydrogenated with high enantioselectivity by an in situ formed chiral ruthenium catalyst. We show that either the ruthenium metathesis catalysts or the ruthenium species formed during the metathesis reaction can be converted into an efficient asymmetric hydrogenation catalyst upon addition of a chiral ligand and an alcohol. The performance in asymmetric hydrogenation appears to be very dependent on the solvent, the chiral ligand, and the prochiral substrate.
Author	Gajewski, Piotr Renom-Carrasco, Marc de Vries, Johannes G. Lefort, Laurent Pignataro, Luca Piarulli, Umberto Gennari, Cesare
Author_xml	– sequence: 1 givenname: Marc surname: Renom-Carrasco fullname: Renom-Carrasco, Marc organization: DSM Innovative Synthesis BV, P. O. Box 18, 6160 MD Geleen, The Netherlands – sequence: 2 givenname: Piotr surname: Gajewski fullname: Gajewski, Piotr organization: DSM Innovative Synthesis BV, P. O. Box 18, 6160 MD Geleen, The Netherlands – sequence: 3 givenname: Luca surname: Pignataro fullname: Pignataro, Luca email: luca.pignataro@unimi.it organization: Università degli Studi di Milano, Dipartimento di Chimica, via C. Golgi 19, 20133 Milan, Italy – sequence: 4 givenname: Johannes G. surname: de Vries fullname: de Vries, Johannes G. email: johannes.devries@catalysis.de organization: Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany – sequence: 5 givenname: Umberto surname: Piarulli fullname: Piarulli, Umberto organization: Università degli Studi dell'Insubria, Dipartimento di Scienza e Alta Tecnologia, via Valleggio 11, 22100 Como, Italy – sequence: 6 givenname: Cesare surname: Gennari fullname: Gennari, Cesare organization: Università degli Studi di Milano, Dipartimento di Chimica, via C. Golgi 19, 20133 Milan, Italy – sequence: 7 givenname: Laurent surname: Lefort fullname: Lefort, Laurent email: laurent.lefort@dsm.com organization: DSM Innovative Synthesis BV, P. O. Box 18, 6160 MD Geleen, The Netherlands
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Keywords	COMPLEXES DECOMPOSITION OLEFIN METATHESIS asymmetric catalysis hydrogenation TETRASUBSTITUTED OLEFINS SOLVENT ruthenium metathesis RING-CLOSING METATHESIS tandem catalysis LIGAND TRANSFORMATIONS
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SSID	ssj0017877
Score	2.213114
Snippet	Here we report the first example of a tandem metathesis–asymmetric hydrogenation protocol where the prochiral olefin generated by metathesis is hydrogenated... Here we report the first example of a tandem metathesis-asymmetric hydrogenation protocol where the prochiral olefin generated by metathesis is hydrogenated...
Source	Web of Science
SourceID	proquest webofscience crossref wiley istex
SourceType	Aggregation Database Enrichment Source Index Database Publisher
StartPage	2223
SubjectTerms	asymmetric catalysis Asymmetry Catalysis Catalysts Chemistry Chemistry, Applied Chemistry, Organic Decomposition reactions Hydrogenation Ligands Metathesis Physical Sciences Ruthenium Science & Technology tandem catalysis
Title	Assisted Tandem Catalysis: Metathesis Followed by Asymmetric Hydrogenation from a Single Ruthenium Source
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