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Synlett 1996; 1996(7): 621-622
DOI: 10.1055/s-1996-5556
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Asymmetric Synthesis of (2S,3S)- and (2R,3S)-2,3-Diaminobutanoic Acids, Non-Protein Amino-Acid Diastereomers found in a number of Peptide Antibiotics

Anthony J. Burke, Stephen G. Davies* , Charles J. R. Hedgecock
  • *The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK
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Publication Date:
31 December 2000 (online)

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(2S,3S)- and (2R,3S)-2,3-diaminobutanoic acids (DABA) are uncommon, naturally occurring amino acid diastereomers found as components of a number of peptide antibiotics. These 2,3-diamino acids have been synthesised by direct and indirect routes, with addition of a chiral lithium amide to tert-butyl crotonate as a key step.

2,3-Diamino acids - lithium amide - conjugate addition - stereocontrol - Mitsunobu reaction

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