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Molecules 2017, 22(10), 1748; doi:10.3390/molecules22101748

Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel–Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester

Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita 9, Nishi 9, Kita-ku, Sapporo 060-8589, Japan
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Received: 28 September 2017 / Revised: 11 October 2017 / Accepted: 13 October 2017 / Published: 17 October 2017
(This article belongs to the Section Organic Synthesis)
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Abstract

Chiral N-protected α-amino aryl-ketones are one of the useful precursors used in the synthesis of various biologically active compounds and can be constructed via Friedel–Crafts acylation of N-protected α-amino acids. One of the drawbacks of this reaction is the utilization of toxic, corrosive and moisture-sensitive acylating reagents. In peptide construction via amide bond formation, N-hydroxysuccinimide ester (OSu), which has high storage stability, can react rapidly with amino components and produces fewer side reactions, including racemization. This study reports the first synthesis and utilization of N-trifluoroacetyl (TFA)-protected α-amino acid-OSu as a potential acyl donor for Friedel–Crafts acylation into various arenes. The TFA-protected isoleucine derivative and its diastereomer TFA-protected allo-isoleucine derivative were investigated to check the retention of α-proton chirality in the Friedel–Crafts reaction. Further utilization of OSu in other branched-chain and unbranched-chain amino acids results in an adequate yield of TFA-protected α-amino aryl-ketone without loss of optical purity. View Full-Text
Keywords: N-hydroxysuccinimide ester; Friedel–Crafts acylation; α-amino acid; α-amino aryl-ketone; racemization N-hydroxysuccinimide ester; Friedel–Crafts acylation; α-amino acid; α-amino aryl-ketone; racemization
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Tachrim, Z.P.; Oida, K.; Ikemoto, H.; Ohashi, F.; Kurokawa, N.; Hayashi, K.; Shikanai, M.; Sakihama, Y.; Hashidoko, Y.; Hashimoto, M. Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel–Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester. Molecules 2017, 22, 1748.

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