Asymmetric Synthesis of Chiral Amino Carboxylic-Phosphonic Acid Derivatives

Chiral amino acids featuring a phosphonate pendant arm are an important type of biologically active scaffold. Here in this review, we comprehensively summarize the modern synthetic methods towards asymmetric construction of chiral amino carboxylic-phosphonic acid derivatives. The main streams of such interesting compounds include phosphono-containing alpha-, beta-, and gamma-amino acid derivatives, amino acid fluorophosphonate derivatives, amino acid cyclopropanylphosphonate derivatives, and bisphosphono-amino acid derivatives. Chiral resolution protocols, chiral auxiliary-directed syntheses, and valorization of the pool of abundant chiral amino acid resources remain contemporary concerns, and meanwhile catalytic enantioselective synthesis has also emerged as a potent strategy as demonstrated by the latest advances.

Automated summary

This review comprehensively summarizes modern synthetic methods towards asymmetric construction of chiral amino carboxylic-phosphonic acid derivatives, including phosphono-containing amino acid derivatives and catalytic enantioselective synthesis as a potent strategy. Topics such as chiral resolution protocols, chiral auxiliary-directed syntheses, and valorization of abundant chiral amino acid resources are also discussed.