Litcius/Paper detail

Ni- and Pd-Catalyzed Enantioselective 1,2-Dicarbofunctionalization of Alkenes

Taeho Kang, Omar Apolinar, Keary M. Engle

2023Synthesis41 citationsDOI

Abstract

Abstract Catalytic enantioselective 1,2-dicarbofunctionalization (1,2-DCF) of alkenes is a powerful transformation of growing importance in organic synthesis for constructing chiral building blocks, bioactive molecules, and agrochemicals. Both in a two- and three-component context, this family of reactions generates densely functionalized, structurally complex products in a single step. Across several distinct mechanistic pathways at play in these transformations with nickel or palladium catalysts, stereocontrol can be obtained through tailored chiral ligands. In this Review we discuss the various strategies, mechanisms, and catalysts that have been applied to achieve enantioinduction in alkene 1,2-DCF. 1 Introduction 2 Two-Component Enantioselective 1,2-DCF via Migratory Insertion 3 Two-Component Enantioselective 1,2-DCF via Radical Capture 4 Three-Component Enantioselective 1,2-DCF via Radical Capture 5 Three-Component Enantioselective 1,2-DCF via Migratory Insertion 6 Miscellaneous Mechanisms 7 Conclusion

Topics & Concepts

Enantioselective synthesisChemistryAlkeneCatalysisCombinatorial chemistryContext (archaeology)Component (thermodynamics)PalladiumMigratory insertionStereochemistryOrganic chemistryPhysicsThermodynamicsBiologyPaleontologyCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsCyclopropane Reaction Mechanisms