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

Wang, Lei; Murai, Yuta; Yoshida, Takuma; Okamoto, Masashi; Tachrim, Zetryana Puteri; Hashidoko, Yasuyuki; Hashimoto, Makoto

doi:10.3390/molecules19056349

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

by

Lei Wang

¹,

Yuta Murai

²,

Takuma Yoshida

¹,

Masashi Okamoto

¹,

Zetryana Puteri Tachrim

¹,

Yasuyuki Hashidoko

¹ and

Makoto Hashimoto

^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.

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

Submission received: 24 April 2014 / Revised: 8 May 2014 / Accepted: 12 May 2014 / Published: 16 May 2014

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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

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MDPI and ACS Style

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. https://doi.org/10.3390/molecules19056349

AMA Style

Wang L, Murai Y, Yoshida T, Okamoto M, Tachrim ZP, 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(5):6349-6367. https://doi.org/10.3390/molecules19056349

Chicago/Turabian Style

Wang, Lei, Yuta Murai, Takuma Yoshida, Masashi Okamoto, Zetryana Puteri Tachrim, Yasuyuki Hashidoko, and Makoto Hashimoto. 2014. "Utilization of Acidic α-Amino Acids as Acyl Donors: An Effective Stereo-Controllable Synthesis of Aryl-Keto α-Amino Acids and Their Derivatives" Molecules 19, no. 5: 6349-6367. https://doi.org/10.3390/molecules19056349

APA Style

Wang, L., Murai, Y., Yoshida, T., Okamoto, M., Tachrim, Z. P., Hashidoko, Y., & Hashimoto, M. (2014). Utilization of Acidic α-Amino Acids as Acyl Donors: An Effective Stereo-Controllable Synthesis of Aryl-Keto α-Amino Acids and Their Derivatives. Molecules, 19(5), 6349-6367. https://doi.org/10.3390/molecules19056349

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

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