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α-C-H Bond Functionalization of Unprotected Alicyclic Amines: Lewis-Acid-Promoted Addition of Enolates to Transient Imines.

ABSTRACT: Enolizable cyclic imines, obtained in situ from their corresponding lithium amides by oxidation with simple ketone oxidants, are readily alkylated with a range of enolates to provide mono- and polycyclic β-aminoketones in a single operation, including the natural product (±)-myrtine. Nitrile anions also serve as competent nucleophiles in these transformations, which are promoted by BF₃ etherate. β-Aminoesters derived from ester enolates can be converted to the corresponding β-lactams.

SUBMITTER: Kim JH

PROVIDER: S-EPMC7924990 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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α-C-H Bond Functionalization of Unprotected Alicyclic Amines: Lewis-Acid-Promoted Addition of Enolates to Transient Imines.

Kim Jae Hyun JH Paul Anirudra A Ghiviriga Ion I Seidel Daniel D

Organic letters 20210119 3

Enolizable cyclic imines, obtained in situ from their corresponding lithium amides by oxidation with simple ketone oxidants, are readily alkylated with a range of enolates to provide mono- and polycyclic β-aminoketones in a single operation, including the natural product (±)-myrtine. Nitrile anions also serve as competent nucleophiles in these transformations, which are promoted by BF<sub>3</sub> etherate. β-Aminoesters derived from ester enolates can be converted to the corresponding β-lactams. ...[more]

PMID: 33464093

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