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

Abstract 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 CF3(CH2)3I. The synthesis was performed on over 100 g scale and can be recommended as the most advanced procedure fo...

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Main Authors:	Zizhen Yin, Dr. Hiroki Moriwaki, Dr. Hidenori Abe, Dr. Toshio Miwa, Dr. Jianlin Han, Prof. Dr. Vadim A. Soloshonok
Format:	Article
Language:	English
Published:	Wiley-VCH 2019-06-01
Series:	ChemistryOpen
Subjects:	asymmetric synthesis amino acids fluorine large-scale synthesis stereochemical outcome
Online Access:	https://doi.org/10.1002/open.201900131

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spelling	doaj-4fdfb45d628045aab656904fd0bacc902021-03-02T09:07:12ZengWiley-VCHChemistryOpen2191-13632019-06-018670170410.1002/open.201900131Large‐Scale Asymmetric Synthesis of Fmoc‐(S)‐2‐Amino‐6,6,6‐Trifluorohexanoic AcidZizhen Yin0Dr. Hiroki Moriwaki1Dr. Hidenori Abe2Dr. Toshio Miwa3Dr. Jianlin Han4Prof. Dr. Vadim A. Soloshonok5College of Chemical Engineering Nanjing Forestry University Nanjing 210037 ChinaHamari Chemicals Ltd. 1-4-29 Kunijima, Higashi-Yodogawa-ku Osaka 533-0024 JapanHamari Chemicals Ltd. 1-4-29 Kunijima, Higashi-Yodogawa-ku Osaka 533-0024 JapanHamari Chemicals Ltd. 1-4-29 Kunijima, Higashi-Yodogawa-ku Osaka 533-0024 JapanCollege of Chemical Engineering Nanjing Forestry University Nanjing 210037 ChinaDepartment of Organic Chemistry I, Faculty of Chemistry University of the Basque Country UPV/EHU Paseo Manuel Lardizábal 3 20018 San Sebastián SpainAbstract 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 CF3(CH2)3I. 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.https://doi.org/10.1002/open.201900131asymmetric synthesisamino acidsfluorinelarge-scale synthesisstereochemical outcome
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Zizhen Yin Dr. Hiroki Moriwaki Dr. Hidenori Abe Dr. Toshio Miwa Dr. Jianlin Han Prof. Dr. Vadim A. Soloshonok
spellingShingle	Zizhen Yin Dr. Hiroki Moriwaki Dr. Hidenori Abe Dr. Toshio Miwa Dr. Jianlin Han Prof. Dr. Vadim A. Soloshonok Large‐Scale Asymmetric Synthesis of Fmoc‐(S)‐2‐Amino‐6,6,6‐Trifluorohexanoic Acid ChemistryOpen asymmetric synthesis amino acids fluorine large-scale synthesis stereochemical outcome
author_facet	Zizhen Yin Dr. Hiroki Moriwaki Dr. Hidenori Abe Dr. Toshio Miwa Dr. Jianlin Han Prof. Dr. Vadim A. Soloshonok
author_sort	Zizhen Yin
title	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_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_sort	large‐scale asymmetric synthesis of fmoc‐(s)‐2‐amino‐6,6,6‐trifluorohexanoic acid
publisher	Wiley-VCH
series	ChemistryOpen
issn	2191-1363
publishDate	2019-06-01
description	Abstract 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 CF3(CH2)3I. 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.
topic	asymmetric synthesis amino acids fluorine large-scale synthesis stereochemical outcome
url	https://doi.org/10.1002/open.201900131
work_keys_str_mv	AT zizhenyin largescaleasymmetricsynthesisoffmocs2amino666trifluorohexanoicacid AT drhirokimoriwaki largescaleasymmetricsynthesisoffmocs2amino666trifluorohexanoicacid AT drhidenoriabe largescaleasymmetricsynthesisoffmocs2amino666trifluorohexanoicacid AT drtoshiomiwa largescaleasymmetricsynthesisoffmocs2amino666trifluorohexanoicacid AT drjianlinhan largescaleasymmetricsynthesisoffmocs2amino666trifluorohexanoicacid AT profdrvadimasoloshonok largescaleasymmetricsynthesisoffmocs2amino666trifluorohexanoicacid
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Large‐Scale Asymmetric Synthesis of Fmoc‐(S)‐2‐Amino‐6,6,6‐Trifluorohexanoic Acid

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