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Enantioselective nickel-catalyzed arylative and alkenylative intramolecular 1,2-allylations of tethered allene-ketones.

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.

SUBMITTER: Di Sanza R

PROVIDER: S-EPMC8157472 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Enantioselective nickel-catalyzed arylative and alkenylative intramolecular 1,2-allylations of tethered allene-ketones.

Di Sanza Riccardo R Nguyen Thi Le Nhon TLN Iqbal Naeem N Argent Stephen P SP Lewis William W Lam Hon Wai HW

Chemical science 20200121 9

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. ...[more]

PMID: 34084403

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