Enantioselective Titanium(III)-Catalyzed Reductive Cyclization of Ketonitriles

Reduction, please! The title reaction affords α‐hydroxyketones, a common structural motif in biologically active natural products, in good yields and high enantioselectivities at room temperature. The commercially available ansa‐titanocene 1 was found to be an efficient catalyst for this process, wh...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 51; no. 34; pp. 8661 - 8664
Main Authors Streuff, Jan, Feurer, Markus, Bichovski, Plamen, Frey, Georg, Gellrich, Urs
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 20.08.2012
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
asymmetric catalysis
Biological activity
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Cyclization
Enantiomers
Ketones - chemistry
Molecular Structure
Natural products
Nitriles
Nitriles - chemistry
Physical Sciences
radical reactions
Radicals
Reduction
Room temperature
Science & Technology
Stereoisomerism
Titanium
Titanium - chemistry
ALPHA-HYDROXY KETONES
ENOL ETHERS
ARYL ALDEHYDES
titanium
radical reactions
SAMARIUM(II) IODIDE
asymmetric catalysis
cyclization
TITANIUM COMPLEXES
LIGANDS
COUPLING REACTIONS
NITRILES
RADICAL CYCLIZATION
reduction
EPOXYNITRILES
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Summary:Reduction, please! The title reaction affords α‐hydroxyketones, a common structural motif in biologically active natural products, in good yields and high enantioselectivities at room temperature. The commercially available ansa‐titanocene 1 was found to be an efficient catalyst for this process, which presumably proceeds by addition of a ketyl radical to a nitrile.
Bibliography:istex:5FF70A8167D2D9B58EE8D3A864F11111DBB02E51
Financial support for this work was provided by the Fonds der Chemischen Industrie and the Deutsche Forschungsgemeinschaft (DFG, STR 1150/3-1).
Deutsche Forschungsgemeinschaft
ArticleID:ANIE201204469
Fonds der Chemischen Industrie
DFG - No. STR 1150/3-1
ark:/67375/WNG-9J76KM6C-M
Financial support for this work was provided by the Fonds der Chemischen Industrie and the Deutsche Forschungsgemeinschaft (DFG, STR 1150/3‐1).
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201204469