Remote Chiral Induction in the Organocatalytic Hydrosilylation of Aromatic Ketones and Ketimines

Lewis basic, metal‐free pyridyloxazolines catalyze the reduction of prochiral aromatic ketones and ketimines with Cl3SiH in good enantioselectivity (up to 94 % ee). Arene–arene interactions between the substrate and the catalyst are likely to play a role in the enantiodifferentiation process.

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Bibliographic Details
Published inAngewandte Chemie (International ed.) Vol. 45; no. 9; pp. 1432 - 1435
Main Authors Malkov, Andrei V., Liddon, Angus J. P. Stewart, Ramírez-López, Pedro, Bendová, Lada, Haigh, David, Kočovský, Pavel
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 20.02.2006
WILEY‐VCH Verlag
Wiley
Subjects
arene-arene interactions
asymmetric catalysis
Catalysis
Chemistry
Chemistry, Multidisciplinary
Computer Simulation
Imines - chemistry
Ketones - chemistry
Molecular Structure
N ligands
organocatalysis
Physical Sciences
reduction
Science & Technology
Silanes - chemistry
Stereoisomerism
STEREOSELECTIVE REDUCTION
IMINES
ENANTIOSELECTIVE REDUCTION
TRANSFER HYDROGENATION
CARBONYL-COMPOUNDS
ALDEHYDES
asymmetric catalysis
TRICHLOROSILANE
organocatalysis
N-OXIDE
N ligands
AMINO-ACIDS
reduction
arene-arene interactions
ASYMMETRIC ALLYLATION
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Summary:Lewis basic, metal‐free pyridyloxazolines catalyze the reduction of prochiral aromatic ketones and ketimines with Cl3SiH in good enantioselectivity (up to 94 % ee). Arene–arene interactions between the substrate and the catalyst are likely to play a role in the enantiodifferentiation process.
Bibliography:We thank the GSK and EPSRC for an industrial CASE awards to A.J.P.S.L., the Ministry of Education and Science of Spain for a postdoctoral fellowship to P.R.-L., the Socrates Exchange program, and Dr. Alfred Bader and the University of Glasgow for an additional support.
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ArticleID:ANIE200503941
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We thank the GSK and EPSRC for an industrial CASE awards to A.J.P.S.L., the Ministry of Education and Science of Spain for a postdoctoral fellowship to P.R.‐L., the Socrates Exchange program, and Dr. Alfred Bader and the University of Glasgow for an additional support.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200503941