Enantioselective nickel-catalyzed arylative and alkenylative intramolecular 1,2-allylations of tethered allene–ketones† † Electronic supplementary information (ESI) available: Experimental procedures, full spectroscopic data for new compounds, and crystallographic data for 2a, 5a, and 5d. CCDC 1945864–1945866. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c9sc05246a

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. Chiral tertiary-alcohol-containing aza- and carbocycles are produced in high diastereo- and enantioselectivities by the nickel-catalyzed reaction of tethered allene–ketones with (hetero)arylboronic acids or potassium vinyltrifluoroborate.

SUBMITTER: Di Sanza R 

PROVIDER: S-EPMC8157472 | biostudies-literature |

REPOSITORIES: biostudies-literature