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A Chiral Naphthyridine Diimine Ligand Enables Nickel‐Catalyzed Asymmetric Alkylidenecyclopropanations

Elena Braconi, Nicolai Cramer

2020Angewandte Chemie International Edition26 citationsDOIOpen Access PDF

Abstract

Abstract A novel class of chiral naphthyridine diimine ligands (NDI*) readily accessible from C 2 ‐symmetric 2,6‐di‐(1‐arylethyl)anilines is described. The utility of these ligands, particularly one with fluorinated aryl side arms, is demonstrated by a reductive Ni‐catalyzed enantioselective alkylidene transfer reaction from 1,1‐dichloroalkenes to olefins. This transformation provides direct access to a broad range of synthetically valuable alkylidenecyclopropanes in high yields and enantioselectivities.

Topics & Concepts

DiimineNickelLigand (biochemistry)CatalysisChemistryCombinatorial chemistryMaterials scienceReceptorOrganic chemistryBiochemistryCyclopropane Reaction MechanismsAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and Catalysis
A Chiral Naphthyridine Diimine Ligand Enables Nickel‐Catalyzed Asymmetric Alkylidenecyclopropanations | Litcius