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Regioselective α-Cyanation of Unprotected Alicyclic Amines.

ABSTRACT: 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.

SUBMITTER: Yu F

PROVIDER: S-EPMC9548390 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Regioselective α-Cyanation of Unprotected Alicyclic Amines.

Yu Fuchao F Valles Daniel A DA Chen Weijie W Daniel Scott D SD Ghiviriga Ion I Seidel Daniel D

Organic letters 20220829 35

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. ...[more]

PMID: 36036764

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