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Synthesis 1999; 1999(3): 423-428
DOI: 10.1055/s-1999-3405
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Friedel-Crafts α-Aminoacylation of Aromatic Compounds with a Chiral N-Carboxy-α-amino Acid Anhydride (NCA); Part 2

Osamu Itoh* , Akira Amano
  • *Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Sakyouku Kyoto 606-8501, Japan; Fax +81(75)7 53 56 97
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Publication Date:
31 December 1999 (online)

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The N-carboxy-α-amino acid anhydrides (NCA) derived from L-Asp(OEt), L-Glu(OMe), L-Met, and L-Pro reacted with aromatic compounds (toluene or benzene) in the presence of AlCl3, to afford the corresponding α-aminoalkyl aryl ketones as hydrochloride salts in moderate yields. The β- and γ-amino acid esters, which were obtained from the reaction of the aromatic compounds with L-Asp(OEt)- and L-Glu(OMe)-NCA, were hydrolyzed by hydrochloric acid to the corresponding β- and γ-amino acids as hydrochloride salts. L-Phe-NCA did not react with benzene in the presence of AlCl3, instead an intramolecular acylation occurred to afford (S)-2-aminoindanone hydrochloride. The chiralities of the original L-α-amino acids were most retained during these α-aminoacylation.

Friedel-Crafts acylation - α-aminoacylation - N-carboxy-α-amino acid anhydride (NCA) - α-aminoalkyl aryl ketone - optically reactive β- and γ-amino acids