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Molecules 2014, 19(5), 6349-6367; doi:10.3390/molecules19056349
Review

Utilization of Acidic α-Amino Acids as Acyl Donors: An Effective Stereo-Controllable Synthesis of Aryl-Keto α-Amino Acids and Their Derivatives

1, 2, 1, 1, 1, 1 and 1,*
1 Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita 9, Nishi 9, Kita-ku, Sapporo 060-8589, Japan 2 Faculty of Advanced Life Science, Frontier Research Center for Post-Genome Science and Technology, Hokkaido University, Kita 21, Nishi 11, Kita-ku, Sapporo 001-0021, Japan
* Author to whom correspondence should be addressed.
Received: 24 April 2014 / Revised: 8 May 2014 / Accepted: 12 May 2014 / Published: 16 May 2014

Abstract

Aryl-keto-containing α-amino acids are of great importance in organic chemistry and biochemistry. They are valuable intermediates for the construction of hydroxyl α-amino acids, nonproteinogenic α-amino acids, as well as other biofunctional components. Friedel-Crafts acylation is an effective method to prepare aryl-keto derivatives. In this review, we summarize the preparation of aryl-keto containing α-amino acids by Friedel-Crafts acylation using acidic α-amino acids as acyl-donors and Lewis acids or Brönsted acids as catalysts.
Keywords: aryl-keto α-amino acid; Friedel-Crafts acylation; Lewis acid; triflic acid aryl-keto α-amino acid; Friedel-Crafts acylation; Lewis acid; triflic acid
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.

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Wang, L.; Murai, Y.; Yoshida, T.; Okamoto, M.; Tachrim, Z.P.; Hashidoko, Y.; Hashimoto, M. Utilization of Acidic α-Amino Acids as Acyl Donors: An Effective Stereo-Controllable Synthesis of Aryl-Keto α-Amino Acids and Their Derivatives. Molecules 2014, 19, 6349-6367.

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