A Chiral Naphthyridine Diimine Ligand Enables Nickel‐Catalyzed Asymmetric Alkylidenecyclopropanations. Issue 38 (10th July 2020)

• Record Type: Journal Article
• Authors: Braconi, Elena; Cramer, Nicolai
• Is Part Of: Angewandte Chemie international edition. Volume 59:Issue 38(2020)
• Page Start: 16425
• Page End: 16429
• Publication Date: 2020-07-10
• Subjects: alkylidene transfer -- asymmetric catalysis -- cyclopropanes -- naphthyridine diimine (NDI) ligands -- nickel; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202006082
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A novel class of chiral naphthyridine diimine ligands (NDI*) readily accessible from C2 ‐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. Abstract : A class of chiral naphthyridine diimine ligands (NDI* ) is described. The application potential of these ligands for asymmetric catalysis is illustrated by a reductive enantioselective bi‐nuclear nickel‐catalyzed alkylidene transfer of 1, 1‐dichloroalkenes to olefins, yielding synthetically valuable alkylidenecyclopropanes in high yields and enantioselectivities.