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Regioselective α-Phosphonylation of Unprotected Alicyclic Amines.

ABSTRACT: Unprotected alicyclic amines undergo α-C-H bond phosphonylation via a two-stage one-pot process involving the oxidation of amine-derived lithium amides with simple ketone oxidants, generating transient imines which are then captured with phosphites or phosphine oxides. Amines with an existing α-substituent undergo regioselective α'-phosphonylation. Amine α-arylation and α'-phosphonylation can be combined, generating a difunctionalized product in a single operation.

SUBMITTER: Li B 

PROVIDER: S-EPMC11289722 | biostudies-literature | 2024 Jul

REPOSITORIES: biostudies-literature

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Regioselective α-Phosphonylation of Unprotected Alicyclic Amines.

Li Bowen B   Yu Fuchao F   Chen Weijie W   Seidel Daniel D  

Organic letters 20240705 28

Unprotected alicyclic amines undergo α-C-H bond phosphonylation via a two-stage one-pot process involving the oxidation of amine-derived lithium amides with simple ketone oxidants, generating transient imines which are then captured with phosphites or phosphine oxides. Amines with an existing α-substituent undergo regioselective α'-phosphonylation. Amine α-arylation and α'-phosphonylation can be combined, generating a difunctionalized product in a single operation. ...[more]

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