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Article

Convenient Asymmetric Synthesis of Fmoc-(S)-6,6,6-Trifluoro-Norleucine

by
Haibo Mei
1,
Zizhen Yin
1,
Toshio Miwa
2,
Hiroki Moriwaki
2,*,
Hidenori Abe
2,
Jianlin Han
1,* and
Vadim A. Soloshonok
3,4,*
1
Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
2
Hamari Chemicals Ltd., 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka 533-0024, Japan
3
Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain
4
IKERBASQUE, Basque Foundation for Science, María Díaz de Haro 3, Plaza Bizkaia, 48013 Bilbao, Spain
*
Authors to whom correspondence should be addressed.
Symmetry 2019, 11(4), 578; https://doi.org/10.3390/sym11040578
Submission received: 8 April 2019 / Revised: 16 April 2019 / Accepted: 18 April 2019 / Published: 21 April 2019
(This article belongs to the Special Issue Amino Acid Chirality)
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Abstract

In this work we report a convenient asymmetric synthesis of Fmoc-(S)-6,6,6-trifluoro-norleucine via alkylation reaction of chiral glycine equivalent. The target amino acid of 99% enantiomeric purity was prepared with 82.4% total yield (three steps).
Keywords: fluorine; amino acids; alkylation; asymmetric synthesis; Ni(II) complexes fluorine; amino acids; alkylation; asymmetric synthesis; Ni(II) complexes

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MDPI and ACS Style

Mei, H.; Yin, Z.; Miwa, T.; Moriwaki, H.; Abe, H.; Han, J.; Soloshonok, V.A. Convenient Asymmetric Synthesis of Fmoc-(S)-6,6,6-Trifluoro-Norleucine. Symmetry 2019, 11, 578. https://doi.org/10.3390/sym11040578

AMA Style

Mei H, Yin Z, Miwa T, Moriwaki H, Abe H, Han J, Soloshonok VA. Convenient Asymmetric Synthesis of Fmoc-(S)-6,6,6-Trifluoro-Norleucine. Symmetry. 2019; 11(4):578. https://doi.org/10.3390/sym11040578

Chicago/Turabian Style

Mei, Haibo, Zizhen Yin, Toshio Miwa, Hiroki Moriwaki, Hidenori Abe, Jianlin Han, and Vadim A. Soloshonok. 2019. "Convenient Asymmetric Synthesis of Fmoc-(S)-6,6,6-Trifluoro-Norleucine" Symmetry 11, no. 4: 578. https://doi.org/10.3390/sym11040578

APA Style

Mei, H., Yin, Z., Miwa, T., Moriwaki, H., Abe, H., Han, J., & Soloshonok, V. A. (2019). Convenient Asymmetric Synthesis of Fmoc-(S)-6,6,6-Trifluoro-Norleucine. Symmetry, 11(4), 578. https://doi.org/10.3390/sym11040578

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