2024-03-28T13:06:38Zhttps://eprints.lib.hokudai.ac.jp/dspace-oai/requestoai:eprints.lib.hokudai.ac.jp:2115/743772022-11-17T02:08:08Zhdl_2115_20046hdl_2115_138Synthesis of chiral N-trifluoroacetyl-methionine derivatives and applying them as acyl donors for Friedel-Crafts acylationKurokawa, NatsumiTokoro, YurikaTachrim, Zetryana PuteriWakasa, Haruna1000010344491Sakihama, Yasuko1000040281795Hashidoko, Yasuyuki1000090292094Hashimoto, Makotoopen accessCreative Commons Attribution-NonCommercial 4.0 InternationalTrifluoroacetamideα-amino acidN-hydroxysuccinimide esterFriedel–Crafts acylationα-amino phenyl ketone430A chiral N-protected α-amino acid N-hydroxysuccinimide ester (OSu) is a common useful reagent for peptide bond formation. Recently, N-trifluoroacetyl (TFA) α-amino acid OSu esters have been reported as acyl donors for Frieldel–Crafts reactions to synthesize chiral α-amino phenyl ketones retaining the configurations of the starting α-amino acids. There are few reports for chiral TFA protected methionine, which has methylthioethyl structure in the side-chain of the α-amino acid. The detailed synthesis of chiral TFA-Met-OSu and its application as an acyl donor for Friedel–Crafts acylation is reported.Arkat-USA2019engjournal articleVoRhttp://hdl.handle.net/2115/74377https://doi.org/10.24820/ark.5550190.p010.8151551-70121551-7004Arkivoc201954249https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/74377/3/19-10815UP_suppl..pdfapplication/pdf6.81 MB2019