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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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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
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author Han, Jianlin
Romoff, Todd T.
Moriwaki, Hiroki
Konno, Hiroyuki
Soloshonok, Vadim A.
author_facet Han, Jianlin
Romoff, Todd T.
Moriwaki, Hiroki
Konno, Hiroyuki
Soloshonok, Vadim A.
author_sort Han, Jianlin
collection PubMed
description [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.
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spelling pubmed-68685922019-11-22 Development of Hamari Ligands for Practical Asymmetric Synthesis of Tailor-Made Amino Acids Han, Jianlin Romoff, Todd T. Moriwaki, Hiroki Konno, Hiroyuki Soloshonok, Vadim A. ACS Omega [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. American Chemical Society 2019-11-07 /pmc/articles/PMC6868592/ /pubmed/31763515 http://dx.doi.org/10.1021/acsomega.9b02940 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Han, Jianlin
Romoff, Todd T.
Moriwaki, Hiroki
Konno, Hiroyuki
Soloshonok, Vadim A.
Development of Hamari Ligands for Practical Asymmetric Synthesis of Tailor-Made Amino Acids
title Development of Hamari Ligands for Practical Asymmetric Synthesis of Tailor-Made Amino Acids
title_full Development of Hamari Ligands for Practical Asymmetric Synthesis of Tailor-Made Amino Acids
title_fullStr Development of Hamari Ligands for Practical Asymmetric Synthesis of Tailor-Made Amino Acids
title_full_unstemmed Development of Hamari Ligands for Practical Asymmetric Synthesis of Tailor-Made Amino Acids
title_short Development of Hamari Ligands for Practical Asymmetric Synthesis of Tailor-Made Amino Acids
title_sort development of hamari ligands for practical asymmetric synthesis of tailor-made amino acids
url 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
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