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Nickel‐Catalyzed Asymmetric Synthesis of α‐Arylbenzamides


Cuesta‐Galisteo, Sergio; Schörgenhumer, Johannes; Wei, Xiaofeng; Merino, Estíbaliz; Nevado, Cristina (2021). Nickel‐Catalyzed Asymmetric Synthesis of α‐Arylbenzamides. Angewandte Chemie Internationale Edition, 60(3):1605-1609.

Abstract

A nickel‐catalyzed asymmetric reductive hydroarylation of vinyl amides to produce enantioenriched α‐arylbenzamides is reported. The use of a chiral bisimidazoline (BIm) ligand, in combination with diethoxymethylsilane and aryl halides, enables the regioselective introduction of aryl groups to the internal position of the olefin, forging a new stereogenic center α to the N atom. The use of neutral reagents and mild reaction conditions provides simple access to pharmacologically relevant motifs present in anticancer, SARS‐CoV PLpro inhibitors, and KCNQ channel openers.

Abstract

A nickel‐catalyzed asymmetric reductive hydroarylation of vinyl amides to produce enantioenriched α‐arylbenzamides is reported. The use of a chiral bisimidazoline (BIm) ligand, in combination with diethoxymethylsilane and aryl halides, enables the regioselective introduction of aryl groups to the internal position of the olefin, forging a new stereogenic center α to the N atom. The use of neutral reagents and mild reaction conditions provides simple access to pharmacologically relevant motifs present in anticancer, SARS‐CoV PLpro inhibitors, and KCNQ channel openers.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Catalysis
Physical Sciences > General Chemistry
Uncontrolled Keywords:General Chemistry, Catalysis
Language:English
Date:18 January 2021
Deposited On:09 Feb 2021 09:48
Last Modified:01 Mar 2022 01:03
Publisher:Wiley-VCH Verlag
ISSN:1433-7851
OA Status:Green
Publisher DOI:https://doi.org/10.1002/anie.202011342
PubMed ID:33015909
Project Information:
  • : FunderFP7
  • : Grant ID307948
  • : Project TitleNIGOCAT - Nature-Inspired Gold Catalytic Tools
  • : FunderSNSF
  • : Grant ID200020_146853
  • : Project TitleNovel Synthetic Methods based on Gold Catalyzed Reactions
  • Content: Accepted Version