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Asymmetric Transfer Hydrogenation of Ketones with Modified Grubbs Metathesis Catalysts: On the Way to a Tandem Process
Author(s) -
RenomCarrasco Marc,
Gajewski Piotr,
Pignataro Luca,
de Vries Johannes G.,
Piarulli Umberto,
Gennari Cesare,
Lefort Laurent
Publication year - 2016
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.201500933
Subject(s) - chemistry , transfer hydrogenation , metathesis , catalysis , acetophenone , enantioselective synthesis , noyori asymmetric hydrogenation , ketone , enantiomeric excess , combinatorial chemistry , salt metathesis reaction , organic chemistry , tandem , ruthenium , polymerization , polymer , materials science , composite material
Herein, we report the successful transformation of a 1 st generation Grubbs metathesis catalyst into an asymmetric transfer hydrogenation (ATH) catalyst. Upon addition of a chiral amine ligand, an alcohol and a base, the 1 st generation Hoveyda–Grubbs catalyst ( HG‐I ) was found to promote the enantioselective reduction of acetophenone to 1‐phenylethanol. After optimizing the order of addition and the reaction conditions, the substrate scope was assessed leading to enantiomeric excesses up to 97% ee . NMR experiments were run in order to get information about the in situ ‐generated ATH catalyst. Furthermore, the possibility to perform olefin metathesis and ketone transfer hydrogenation sequentially in one pot was demonstrated, and the first tandem olefin metathesis–ketone asymmetric transfer hydrogenation was carried out.