Enantioselective nickel-catalyzed arylative and alkenylative intramolecular 1,2-allylations of tethered allene–ketones
Riccardo Di Sanza, Thi Le Nhon Nguyen, Naeem Iqbal, Stephen P. Argent, William Lewis, Hon Wai Lam
Abstract
The enantioselective nickel-catalyzed reaction of tethered allene-ketones with (hetero)arylboronic acids or potassium vinyltrifluoroborate is described. Carbonickelation of the allene gives allylnickel species, which undergo cyclization by 1,2-allylation to produce chiral tertiary-alcohol-containing aza- and carbocycles in high diastereo- and enantioselectivities.
Topics & Concepts
Enantioselective synthesisIntramolecular forceAlleneCatalysisChemistryNickelStereochemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalytic C–H Functionalization MethodsAsymmetric Synthesis and CatalysisCyclopropane Reaction Mechanisms