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Synlett 1990; 1990(12): 735-736
DOI: 10.1055/s-1990-21230
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An Approach to the Synthesis of Enantiomerically Pure Hydroxylated α-Amino Acids Using Zinc Homoenolate Chemistry

Richard F. W. Jackson* , Anthony Wood, Martin J. Wythes
  • *Department of Chemistry, Bedson Building, The University, Newcastle upon Tyne, NE1 7RU, England
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Publication Date:
08 March 2002 (online)

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Diastereoselective reduction of enantiomerically pure 4-oxo α-amino acids, available from the reaction of the zinc homoenolate 1 [(S)-N-(tert-butoxycarbonyl)-3-iodozincioalanine benzyl ester] with α-functionalised acetyl chlorides in the presence of bis(triphenylphosphine)palladium dichloride, allows the preparation of a variety of 4-hydroxy α-amino acid derivatives, including the potential clavalanine precursor 5a and the erythro 4-hydroxyornithine derivative 6f.

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