Easy access to constrained peptidomimetics and 2,2-disubstituted azetidines by the unexpected reactivity profile of α-lithiated N-Boc-azetidines

作者: Giovanna Parisi , Emanuela Capitanelli , Antonella Pierro , Giuseppe Romanazzi , Guy J. Clarkson

DOI: 10.1039/C5CC06323J

关键词: ChemistryPeptidomimeticRegioselectivityReactivity (chemistry)MoleculeStereochemistryAzetidineStereoisomerismRing (chemistry)

摘要: The reactivity profile of lithiated N-Boc-2-arylazetidines has been investigated filling a gap in the chemistry this class four-membered heterocycles. Two unexpected and unprecedented results have observed: an “ortho-effect” accounting for regioselective functionalization azetidine ring, self-condensation leading to new interesting azetidine-based peptidomimetics.

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