Palladium-Catalyzed sp3 C–H Acetoxylation of α,α-Disubstituted α-Amino Acids

The sp3 C–H acetoxylation at the β-position of α,α-disubstituted α-amino acids proceeds smoothly under palladium catalysis in the presence of PhI(OAc)2. This reaction provides a straightforward synthetic route to non-natural β-acetoxy-α-amino acids. The reaction of α-aminocyclopropanecarboxylic acid...

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Bibliographic Details
Published inChemistry an international journal Vol. 5; no. 2; pp. 1369 - 1377
Main Authors Matsumura, Atsushi, Usuki, Yoshinosuke, Satoh, Tetsuya
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.06.2023
Subjects
acetoxylation
Amino acids
Chromatography
Crystallography
C–H functionalization
Efficiency
Ligands
Natural products
Palladium
Ring opening
α-amino acid
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Summary:The sp3 C–H acetoxylation at the β-position of α,α-disubstituted α-amino acids proceeds smoothly under palladium catalysis in the presence of PhI(OAc)2. This reaction provides a straightforward synthetic route to non-natural β-acetoxy-α-amino acids. The reaction of α-aminocyclopropanecarboxylic acid takes place via ring-opening to selectively afford an acyclic γ-acetoxy-α,β-unsaturated amino acid.
ISSN:2624-8549
2624-8549
DOI:10.3390/chemistry5020093