4.8 Article

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

Journal

ORGANIC LETTERS
Volume 23, Issue 3, Pages 797-801

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c04024

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Funding

  1. NIH-NIGMS [R01GM101389]
  2. NIH [S10 OD021758-01A1]

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

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