Opportunities Offered by Chiral η6-AreneN-Arylsulfonyl-diamine-RuII Catalysts in the Asymmetric Transfer Hydrogenation of Ketones and Imines 英文参考文献.docVIP
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Opportunities Offered by Chiral η6-AreneN-Arylsulfonyl-diamine-RuII Catalysts in the Asymmetric Transfer Hydrogenation of Ketones and Imines 英文参考文献
Molecules 2011, 16, 5460-5495; doi:10.3390/moleculeOPEN ACCESS
molecules
ISSN 1420-3049
/journal/molecules
Review
Opportunities Offered by Chiral η6-Arene/N-Arylsulfonyl-
diamine-RuII Catalysts in the Asymmetric Transfer
Hydrogenation of Ketones and Imines
Ji?í Václavík 1, Petr Ka?er 1,*, Marek Kuzma 2 and Libor ?erveny 1
1
Department of Organic Technology, Institute of Chemical Technology, Technická 5, CZ-166 28
Prague, Czech Republic
2
Laboratory of Molecular Structure Characterization, Institute of Microbiology, v.v.i., Academy of
Sciences of the Czech Republic, Vídeňská 1083, CZ-142 20, Prague, Czech Republic
* Author to whom correspondence should be addressed; E-Mail: petr.kacer@vscht.cz;
Tel.: +420-220-444-158; Fax: +420-220-444-340.
Received: 25 May 2011; in revised form: 14 June 2011 / Accepted: 17 June 2011 /
Published: 28 June 2011
Abstract: Methods for the asymmetric transfer hydrogenation (ATH) of ketones and
imines are still being intensively studied and developed. Of foremost interest is the use of
Noyori’s [RuCl(η6-arene)(N-TsDPEN)] complexes in the presence of a hydrogen donor
(i-PrOH, formic acid). These complexes have found numerous practical applications and
have been extensively modified. The resulting derivatives have been heterogenized, used in
ATH in water or ionic liquids and even some attempts have been made to approach the
properties of biocatalysts. Therefore, an appropriate modification of the catalyst that suits
the specific requirements for the reaction conditions is very often readily available. The
mechanism of the reaction has also been explored to a great extent. Model substrates,
acetophenone (a ketone) and 6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline (an imine),
are both reduced by this Ru catalytic system with almost perfect selectivity. However, in
each case the major product is a different enantiomer (S- for an alcohol, R- for an amine
when t
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