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A Novel Example of Chiral Counteranion Induced Enantioselective Metal Catalysis: The Importance of Ion-Pairing in Copper-Catalyzed Olefin Aziridination and Cyclopropanation

2000/12/01 by David B. Llewellyn, Dan Adamson, Bruce A. Arndtsen · 3 citations
Chemistry · #Synthesis and Catalytic Reactions #Asymmetric Hydrogenation and Catalysis #Cyclopropane Reaction Mechanisms

paper · doi:10.1021/ol000303y

openalex publication_date 2000/12/01 · openalex created_date 2016/06/24 · openalex updated_date 2026/08/01

Abstract

A new ion-pairing route to achieve asymmetric catalysis has been observed in the copper-catalyzed aziridination of styrene with a chiral counteranion. Structural studies suggest that enantioinduction occurs via ion-pairing of the cationic copper catalyst in the chiral pocket created by the anion. The degree of asymmetric induction can be tuned with features that affect ion-pairing, such as achiral and chiral ligands, temperature, and solvent polarity.

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