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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Vydané v:	Advanced synthesis & catalysis Ročník 357; číslo 10; s. 2223 - 2228
Hlavní autori:	Renom-Carrasco, Marc, Gajewski, Piotr, Pignataro, Luca, de Vries, Johannes G., Piarulli, Umberto, Gennari, Cesare, Lefort, Laurent
Médium:	Journal Article
Jazyk:	English
Vydavateľské údaje:	Weinheim WILEY-VCH Verlag 06.07.2015 WILEY‐VCH Verlag Wiley
Predmet:	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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Popis
Shrnutí:	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.
Bibliografia:	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