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Enantio- and Regioconvergent Nickel-Catalyzed C(sp³ )-C(sp³ ) Cross-Coupling of Allylic Electrophiles Steered by a Silyl Group.

ABSTRACT: A two-step sequence for the enantio- and diastereoselective synthesis of exclusively alkyl-substituted acyclic allylic systems with a stereocenter in the allylic position is reported. The asymmetric induction and the site selectivity are controlled in an enantio- and regioconvergent nickel-catalyzed C(sp³ )-C(sp³ ) cross-coupling of regioisomeric mixtures of racemic α-/γ-silylated allylic halides and primary alkylzinc reagents. The silyl group steers the allylic displacement towards the formation of the vinylsilane regioisomer, and the resulting C(sp² )-Si bond serves as a linchpin for the installation of various C(sp³ ) substituents in a subsequent step.

SUBMITTER: Kranidiotis-Hisatomi N

PROVIDER: S-EPMC8251714 | biostudies-literature |

REPOSITORIES: biostudies-literature

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