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Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Hao‐Qiang Cao, Jun‐Kuan Li, Fa‐Guang Zhang, Dominique Cahard, Jun‐An Ma

2020Advanced Synthesis & Catalysis36 citationsDOIOpen Access PDF

Abstract

Abstract 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 α‐, β‐, and γ‐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. magnified image

Topics & Concepts

Enantioselective synthesisChemistryPhosphonateAmino acidCarboxylic acidEnantiomerCatalysisOptically activeOrganic chemistryCombinatorial chemistryStereochemistryBiochemistryOrganophosphorus compounds synthesisChemical Synthesis and AnalysisAsymmetric Hydrogenation and Catalysis
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