Interrupted Polonovski Strategy for the Synthesis of Functionalized Amino Acids and Peptides

The α-functionalization of carbamate-protected hydroxylamine glycine derivatives, acting as imine surrogates via an interrupted Polonovski reaction, is described to access functionalized amino acid derivatives. The addition of C, N, O, and S nucleophiles was achieved in a one-pot procedure in 37% to...

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Bibliographic Details
Published in:Organic letters 2024-01, Vol.26 (2), p.456-460
Main Authors: Marty, Christine, Allouche, Emmanuelle M. D., Waser, Jerome
Format: Article
Language:English
Subjects:
Amines
Amino Acids - chemistry
Dipeptides - chemistry
Glycine - chemistry
Peptides
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Summary:The α-functionalization of carbamate-protected hydroxylamine glycine derivatives, acting as imine surrogates via an interrupted Polonovski reaction, is described to access functionalized amino acid derivatives. The addition of C, N, O, and S nucleophiles was achieved in a one-pot procedure in 37% to 92% yield. This method could be extended to dipeptide derivatives for the functionalization of both the C-terminus and N-terminus.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03603