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Synlett 1999; 1999(4): 459-461
DOI: 10.1055/s-1999-2627
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Optically Active Precursors for Quaternary Amino Acids by Addition of N-Heteroaromatics to 3-Alkylidene-2,5-diketopiperazines

Shangde Jin* , Jürgen Liebscher
  • *Institut für Chemie, Humboldt-Universität Berlin, Hessische Str. 1-2, D-10115 Berlin, Germany; Fax +49(30)20 93 90 39; E-mail: liebscher@chemie.hu-berlin.de
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Publication Date:
31 December 1999 (online)

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Addition of N-heteroaromatics 3 to 3-alkylidene or 3-benzylidene-2,4-diketopiperazines 1 in the presence of catalytic amounts of HBr gave access to optically active 3-alkyl-2,5-diketopiperazines 4 as potential precursors for quaternary α-amino acids. In addition, unexpected migrations of the C-C-double bonds were observed leading to racemic 6-alkylidene-2,5-diketopiperazines 6 and 3,6-dialkyl-2,5-diketopiperazines 7.

diketopiperazines - 3-alkylidene-diketopiperazines - amino acids - isomerisation