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Updated: Jan 20, 2026
Amino acids: Structure, Classification, D- & L-Isomers
Brønsted Acid-Catalyzed Epimerization-Free Preparation of Dual-Protected Amino Acid Derivatives
Pedro P de Castro1, Isabela M R Rimulo1, Angelina M de Almeida1
1Department of Chemistry, Federal University of Juiz de Fora, Campus Martelos, Juiz de Fora, Minas Gerais 36036-900, Brazil.
Abstract:
An organocatalytic protocol, employing the commercially available EDC as coupling agent, has been developed for the preparation of dual-protected amino acid derivatives without epimerization. This methodology was then applied to different Boc-amino acid and amine derivatives in moderate to excellent isolated yields. In addition, racemization-free Boc deprotection was also demonstrated. Mechanism investigation through electrospray ionization (+)-mass spectrometry/mass spectrometry revealed an acyclic intermediate (no azlactone formation) activated by the camphorsulfonic acid as an organocatalyst as a key step for the sequential attack of the nucleophile.
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