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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Bibliographic Details
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
Online Access:Get full text
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Summary: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.
Bibliography:istex:51E83E9C388225A5A294846DA233EDC83AA55136
European Commission - No. ITN-EID "REDUCTO" PITN-GA-2012-316371
ark:/67375/WNG-FWMTPWCP-S
ArticleID:ADSC201500359
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201500359