Large‐Scale Asymmetric Synthesis of Fmoc‐(S)‐2‐Amino‐6,6,6‐Trifluorohexanoic Acid

Here we report the first large‐scale synthesis of Fmoc‐(S)‐2‐amino‐6,6,6‐trifluorohexanoic acid via asymmetric alkylation of chiral Ni(II)‐complex of glycine Schiff base with CF(3)(CH(2))(3)I. The synthesis was performed on over 100 g scale and can be recommended as the most advanced procedure for r...

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Detalles Bibliográficos
Autores principales: Yin, Zizhen, Moriwaki, Hiroki, Abe, Hidenori, Miwa, Toshio, Han, Jianlin, Soloshonok, Vadim A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6554705/
https://www.ncbi.nlm.nih.gov/pubmed/31183311
http://dx.doi.org/10.1002/open.201900131
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author Yin, Zizhen
Moriwaki, Hiroki
Abe, Hidenori
Miwa, Toshio
Han, Jianlin
Soloshonok, Vadim A.
author_facet Yin, Zizhen
Moriwaki, Hiroki
Abe, Hidenori
Miwa, Toshio
Han, Jianlin
Soloshonok, Vadim A.
author_sort Yin, Zizhen
collection PubMed
description Here we report the first large‐scale synthesis of Fmoc‐(S)‐2‐amino‐6,6,6‐trifluorohexanoic acid via asymmetric alkylation of chiral Ni(II)‐complex of glycine Schiff base with CF(3)(CH(2))(3)I. The synthesis was performed on over 100 g scale and can be recommended as the most advanced procedure for reliable preparation of large amounts of enantiomerically pure Fmoc‐(S)‐2‐amino‐6,6,6‐trifluorohexanoic acid for protein engineering and drug design. Chiral auxiliary used in this protocol can be >90 % recovered and reused.
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spelling pubmed-65547052019-06-10 Large‐Scale Asymmetric Synthesis of Fmoc‐(S)‐2‐Amino‐6,6,6‐Trifluorohexanoic Acid Yin, Zizhen Moriwaki, Hiroki Abe, Hidenori Miwa, Toshio Han, Jianlin Soloshonok, Vadim A. ChemistryOpen Communications Here we report the first large‐scale synthesis of Fmoc‐(S)‐2‐amino‐6,6,6‐trifluorohexanoic acid via asymmetric alkylation of chiral Ni(II)‐complex of glycine Schiff base with CF(3)(CH(2))(3)I. The synthesis was performed on over 100 g scale and can be recommended as the most advanced procedure for reliable preparation of large amounts of enantiomerically pure Fmoc‐(S)‐2‐amino‐6,6,6‐trifluorohexanoic acid for protein engineering and drug design. Chiral auxiliary used in this protocol can be >90 % recovered and reused. John Wiley and Sons Inc. 2019-06-07 /pmc/articles/PMC6554705/ /pubmed/31183311 http://dx.doi.org/10.1002/open.201900131 Text en ©2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Yin, Zizhen
Moriwaki, Hiroki
Abe, Hidenori
Miwa, Toshio
Han, Jianlin
Soloshonok, Vadim A.
Large‐Scale Asymmetric Synthesis of Fmoc‐(S)‐2‐Amino‐6,6,6‐Trifluorohexanoic Acid
title Large‐Scale Asymmetric Synthesis of Fmoc‐(S)‐2‐Amino‐6,6,6‐Trifluorohexanoic Acid
title_full Large‐Scale Asymmetric Synthesis of Fmoc‐(S)‐2‐Amino‐6,6,6‐Trifluorohexanoic Acid
title_fullStr Large‐Scale Asymmetric Synthesis of Fmoc‐(S)‐2‐Amino‐6,6,6‐Trifluorohexanoic Acid
title_full_unstemmed Large‐Scale Asymmetric Synthesis of Fmoc‐(S)‐2‐Amino‐6,6,6‐Trifluorohexanoic Acid
title_short Large‐Scale Asymmetric Synthesis of Fmoc‐(S)‐2‐Amino‐6,6,6‐Trifluorohexanoic Acid
title_sort large‐scale asymmetric synthesis of fmoc‐(s)‐2‐amino‐6,6,6‐trifluorohexanoic acid
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6554705/
https://www.ncbi.nlm.nih.gov/pubmed/31183311
http://dx.doi.org/10.1002/open.201900131
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