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Iron-Catalyzed Synthesis of α-Azido α-Amino Esters via the Alkylazidation of Alkenes.

ABSTRACT: An iron-catalyzed alkylazidation of dehydroamino acids using peroxides as alkyl radical precursors is described. Non-natural azidated amino esters bearing an α-alkyl chain could be obtained in 18-94% yields using TMSN₃ as an azide source. The obtained α-alkyl-α-azide α-amino esters could be further functionalized through cycloaddition or azide reduction with amide couplings to afford aminal-type peptides, α-triazolo amino acids, and tetrahydro-triazolopyridine, showing the great versatility of this now easily accessible class of amino acids.

SUBMITTER: Palamini P

PROVIDER: S-EPMC10521020 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature

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Iron-Catalyzed Synthesis of α-Azido α-Amino Esters via the Alkylazidation of Alkenes.

Palamini Pierre P Allouche Emmanuelle M D EMD Waser Jerome J

Organic letters 20230908 37

An iron-catalyzed alkylazidation of dehydroamino acids using peroxides as alkyl radical precursors is described. Non-natural azidated amino esters bearing an α-alkyl chain could be obtained in 18-94% yields using TMSN<sub>3</sub> as an azide source. The obtained α-alkyl-α-azide α-amino esters could be further functionalized through cycloaddition or azide reduction with amide couplings to afford aminal-type peptides, α-triazolo amino acids, and tetrahydro-triazolopyridine, showing the great versa ...[more]

PMID: 37684011

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