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An efficient method for the synthesis of enantiopure ω-amino acids with proteinogenic side chains

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An efficient method for the synthesis of enantiopure ω-amino acids with proteinogenic side chains
Noula, C. Loukas, V. Kokotos, G.
scientific_publication_article
Επιστημονική δημοσίευση - Άρθρο Περιοδικού (EL)
Scientific publication - Journal Article (EN)
2002
An efficient method for the synthesis of enantiopure ω-amino acids with proteinogenic side chains, starting from the corresponding natural α-amino acids, was developed. N-Protected amino aldehydes, obtained from the corresponding amino alcohols by oxidation with NaOCl in the presence of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-yloxy free radical (AcNH-TEMPO), reacted with the ylides generated from TrO(CH2)nP+Ph3I-. Catalytic hydrogenation produced N-protected ω-amino alcohols. Boc-Protected ω-amino acids were obtained in high yields by the oxidation of these alcohols using NaOCl in the presence of a catalytic amount of AcNH-TEMPO and Bu4N+HSO4-. The present route to ω-amino acids permits the insertion of any chain length between the amino and carboxy functionalities depending on the chain length of the starting ylide used for the Wittig olefination reaction. (EN)
English
https://creativecommons.org/licenses/by-nc/4.0/
University of Athens
Pergamos Digital Library
Journal Article



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