posted on 2019-01-16, 21:14authored byHaibo Mei, Takahiro Hiramatsu, Ryosuke Takeda, Hiroki Moriwaki, Hidenori Abe, Jianlin Han, Vadim A. Soloshonok
Here
we disclose a practical asymmetric synthesis of an enantiomerically
97.8% ee pure N-Fmoc derivative of (S)-2-amino-4,4,4-trifluorobutanoic acid performed on >10 g scale
of
the target product. The method is based on alkylation (CF3–CH2–I) of a new generation of a chiral
nucleophilic equivalent conducted at ambient temperature with an excellent
stereochemical outcome. The developed protocol does not require any
chromatographic separations and includes only one purification step
via recrystallization of the final product.