Asymmetric Iron‐Catalyzed C−H Alkylation Enabled by Remote Ligand meta‐Substitution

Highly enantioselective iron‐catalyzed C−H alkylations by inner‐sphere C−H activation were accomplished with ample scope. High levels of enantiocontrol proved viable through a novel ligand design that exploits a remote meta‐substitution on N‐heterocyclic carbenes within a facile ligand‐to‐ligand H‐t...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 56; no. 45; pp. 14197 - 14201
Main Authors Loup, Joachim, Zell, Daniel, Oliveira, João C. A., Keil, Helena, Stalke, Dietmar, Ackermann, Lutz
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 06.11.2017
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Alkylation
asymmetric catalysis
Carbenes
Chemistry
Chemistry, Multidisciplinary
chiral ligands
C−H activation
Enantiomers
Iron
Ligands
metallocene
Physical Sciences
Science & Technology
CINNAMYL DERIVATIVES
metallocene
CARBOLITHIATION
REACTIVITY
CRYSTAL-STRUCTURES
asymmetric catalysis
chiral ligands
C-H activation
AMINES
MEDIATED METALATION
SYNTHETIC APPLICATIONS
iron
LITHIUM
LITHIATION
AMIDES
C−H activation
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Summary:Highly enantioselective iron‐catalyzed C−H alkylations by inner‐sphere C−H activation were accomplished with ample scope. High levels of enantiocontrol proved viable through a novel ligand design that exploits a remote meta‐substitution on N‐heterocyclic carbenes within a facile ligand‐to‐ligand H‐transfer C−H cleavage. Remote for Fe: Asymmetric iron‐catalyzed C−H alkylations were realized through a novel ligand design featuring remote meta‐substitution for organometallic C−H activation (see scheme; PMP=para‐methoxyphenyl, Ad=adamantyl).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201709075