Insight into and Practical Application of pH-Controlled Asymmetric Transfer Hydrogenation of Aromatic Ketones in Water

Much faster, more enantioselective, and more‐productive catalysis was attained in the asymmetric transfer hydrogenation of aromatic ketones with the Noyori–Ikariya Ru–Ts‐dpen catalyst in water under slightly basic conditions (see scheme). At low pH values, the reaction was much less efficient and ap...

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Published inAngewandte Chemie (International ed.) Vol. 44; no. 22; pp. 3407 - 3411
Main Authors Wu, Xiaofeng, Li, Xiaoguang, King, Frank, Xiao, Jianliang
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 30.05.2005
WILEY‐VCH Verlag
Wiley
Subjects
acidity
asymmetric catalysis
Chemistry
Chemistry, Multidisciplinary
ketones
Physical Sciences
ruthenium
Science & Technology
transfer hydrogenation
FORMIC-ACID
BIPHASIC TRANSFER HYDROGENATION
AQUEOUS-MEDIA
COMPLEXES
transfer hydrogenation
CARBONYL-COMPOUNDS
asymmetric catalysis
CATALYST
ketones
ALCOHOLS
ruthenium
acidity
LIGANDS
DIAMINE
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Summary:Much faster, more enantioselective, and more‐productive catalysis was attained in the asymmetric transfer hydrogenation of aromatic ketones with the Noyori–Ikariya Ru–Ts‐dpen catalyst in water under slightly basic conditions (see scheme). At low pH values, the reaction was much less efficient and appears to operate through a different mechanism.
Bibliography:ArticleID:ANIE200500023
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istex:09678AE1DC3FC114AC7AA4EF70A83A97FAEB12A9
We thank the DTI MMI project and its industrial/academic partners (Prof. R. Catlow, Royal Institution; Dr. A. Danopoulos, University of Southampton; Dr. F. Hancock and Dr. A. Zanotti-Gerosa, Johnson Matthey; Dr. P. Levett and Dr. A. Pettman, Pfizer; Dr. P. Hogan and Dr. M. Purdie, AstraZeneca; Dr. P. Ravenscroft, GlaxoSmithKline) for financial support and valuable suggestions. We also thank Dr. N. Winterton for helpful suggestions.
We thank the DTI MMI project and its industrial/academic partners (Prof. R. Catlow, Royal Institution; Dr. A. Danopoulos, University of Southampton; Dr. F. Hancock and Dr. A. Zanotti‐Gerosa, Johnson Matthey; Dr. P. Levett and Dr. A. Pettman, Pfizer; Dr. P. Hogan and Dr. M. Purdie, AstraZeneca; Dr. P. Ravenscroft, GlaxoSmithKline) for financial support and valuable suggestions. We also thank Dr. N. Winterton for helpful suggestions.
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SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200500023