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Regioselective α-Cyanation of Unprotected Alicyclic Amines. 2022

Fuchao Yu, and Daniel A Valles, and Weijie Chen, and Scott D Daniel, and Ion Ghiviriga, and Daniel Seidel
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.

Secondary alicyclic amines are converted to α-aminonitriles via addition of TMSCN to their corresponding imines, intermediates that are produced in situ via the oxidation of amine-derived lithium amides with simple ketone oxidants. Amines with an existing α-substituent undergo regioselective α'-cyanation even if the C-H bonds at that site are less activated. Amine α-arylation can be combined with α'-cyanation to generate difunctionalized products in a single operation.

UI MeSH Term Description Entries

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