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Development of Hamari Ligands for Practical Asymmetric Synthesis of Tailor-Made Amino Acids

[Image: see text] Enantiomerically pure tailor-made amino acids are in extremely high demand in nearly every sector of the health-related industries. In particular, the rapidly growing number of amino-acid-based pharmaceuticals calls for the development of advanced synthetic approaches featuring pra...

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Detalles Bibliográficos
Autores principales: Han, Jianlin, Romoff, Todd T., Moriwaki, Hiroki, Konno, Hiroyuki, Soloshonok, Vadim A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6868592/
https://www.ncbi.nlm.nih.gov/pubmed/31763515
http://dx.doi.org/10.1021/acsomega.9b02940
Descripción
Sumario:[Image: see text] Enantiomerically pure tailor-made amino acids are in extremely high demand in nearly every sector of the health-related industries. In particular, the rapidly growing number of amino-acid-based pharmaceuticals calls for the development of advanced synthetic approaches featuring practicality and commercial viability. Here we provide a brief summary of the development of axially chiral tridentate Hamari ligands and their application for general asymmetric synthesis of various structural types of amino acids. The methodological diversity includes: dynamic kinetic resolution and (S)-/(R)-interconversion of unprotected amino acids and homologation of nucleophilic glycine equivalents via alkyl halide alkylation reactions as well as multiple-step transformations allowing preparation of polyfunctional and cyclic derivatives. The practicality of these methods is critically discussed.