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α-Functionalization of Cyclic Secondary Amines: Lewis Acid Promoted Addition of Organometallics to Transient Imines

  • Anirudra Paul
    Anirudra Paul
    Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States
  •  and 
  • Daniel Seidel*
    Daniel Seidel
    Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States
    *[email protected]
Cite this: J. Am. Chem. Soc. 2019, 141, 22, 8778–8782
Publication Date (Web):May 22, 2019
https://doi.org/10.1021/jacs.9b04325
Copyright © 2019 American Chemical Society

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    Abstract

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    Cyclic imines, generated in situ from their corresponding N-lithiated amines and a ketone hydride acceptor, undergo reactions with a range of organometallic nucleophiles to generate α-functionalized amines in a single operation. Activation of the transient imines by Lewis acids that are compatible with the presence of lithium alkoxides was found to be crucial to accommodate a broad range of nucleophiles including lithium acetylides, Grignard reagents, and aryllithiums with attenuated reactivities.

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