Direct N-alkylation of unprotected amino acids with alcohols.

ABSTRACT: 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 ?-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 ?-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.

SUBMITTER: Yan T 

PROVIDER: S-EPMC5722651 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature