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 May 16;19(5):6349-67. doi: 10.3390/molecules19056349.

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Acylation
  • Amino Acids, Acidic / chemistry*
  • Amino Acids, Acidic / metabolism
  • Catalysis
  • Lewis Acids / chemistry*
  • Lewis Acids / metabolism
  • Mesylates / chemistry*
  • Mesylates / metabolism

Substances

  • Amino Acids, Acidic
  • Lewis Acids
  • Mesylates
  • trifluoromethanesulfonic acid