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Assisted Tandem Catalysis: Metathesis Followed by Asymmetric Hydrogenation from a Single Ruthenium Source
Author(s) -
RenomCarrasco Marc,
Gajewski Piotr,
Pignataro Luca,
de Vries Johannes G.,
Piarulli Umberto,
Gennari Cesare,
Lefort Laurent
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500359
Subject(s) - ruthenium , chemistry , metathesis , asymmetric hydrogenation , catalysis , noyori asymmetric hydrogenation , salt metathesis reaction , tandem , enantioselective synthesis , combinatorial chemistry , ligand (biochemistry) , ring opening metathesis polymerisation , ring closing metathesis , organic chemistry , polymerization , materials science , biochemistry , receptor , composite material , polymer
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.