Development of Hamari Ligands for Practical Asymmetric Synthesis of Tailor-Made Amino Acids.
| Autor: | Han J; College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China., Romoff TT; Hamari Chemicals USA, San Diego, California 92121, United States., Moriwaki H; Hamari Chemicals Ltd., 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka 533-0024, Japan., Konno H; Department of Biochemical Engineering, Graduate School of Science and Engineering, Yamagata University, Yonezawa, Yamagata 992-8510, Japan., Soloshonok VA; Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain.; IKERBASQUE, Basque Foundation for Science, María Díaz de Haro 3, Plaza Bizkaia, 48013 Bilbao, Spain. |
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| Jazyk: | angličtina |
| Zdroj: | ACS omega [ACS Omega] 2019 Nov 07; Vol. 4 (21), pp. 18942-18947. Date of Electronic Publication: 2019 Nov 07 (Print Publication: 2019). |
| DOI: | 10.1021/acsomega.9b02940 |
| Abstrakt: | 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. Competing Interests: The authors declare no competing financial interest. (Copyright © 2019 American Chemical Society.) |
| Databáze: | MEDLINE |
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