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
Descripción
Sumario: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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