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Paper | Special issue | Vol 97, No. 2, 2018, pp.877-893
Published online, 14th May, 2018
DOI: 10.3987/COM-18-S(T)65
TFA-Protected α-Amino Acid N-Hydroxysuccinimide Ester: Application for Inter- and Intramolecular Acylation

Zetryana Puteri Tachrim, Kazuhiro Oida, Fumina Ohashi, Haruna Wakasa, Haruka Ikemoto, Natsumi Kurokawa, Yasuko Sakihama, Yasuyuki Hashidoko, Takeyuki Suzuki, and Makoto Hashimoto*

*Graduate School of Agriculture, Hokkaido University, Kita 9 Nishi 9, Kita-ku, Sapporo, Hokkaido 060-0589, Japan


The utilization of N-trifluoroacetyl (TFA)-α-amino acid N-hydroxysuccinimide ester (OSu) derivatives, a promising acylating agent with high storage stability, is reported for Friedel–Crafts acylation into arenes and N-heterocycles. The reaction between TFA-Phe-OSu derivatives and arenes afforded inter- and intramolecular products. TFA-Tyr-OSu derivatives, which possess hydroxyl substituent in the aromatic moiety of phenylalanine, afforded only intermolecular product with benzene. The heterocyclic TFA-Pro-OSu also shows relatively high reactivity toward acylation.