Direct N-alkylation of unprotected amino acids with alcohols

Yan, T., Feringa, B. L. & Barta, K., Dec-2017, In : Science Advances. 3, 12, 7 p., eaao6494.

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N-alkyl amino acids find widespread application as highly valuable, renewable building blocks. However, traditional synthesis methodologies to obtain these suffer from serious limitations, providing a major challenge to develop sustainable alternatives. We report the first powerful catalytic strategy for the direct N-alkylation of unprotected a-amino acids with alcohols. This method is highly selective, produces water as the only side product leading to a simple purification procedure, and a variety of alpha-amino acids are mono- or di-N-alkylated, in most cases with excellent retention of optical purity. The hydrophobicity of the products is tunable, and even simple peptides are selectively alkylated. An iron-catalyzed route to mono-N-alkyl amino acids using renewable fatty alcohols is also described that represents an ideal green transformation for obtaining fully bio-based surfactants.

Original languageEnglish
Article numbereaao6494
Number of pages7
JournalScience Advances
Issue number12
Publication statusPublished - Dec-2017


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