An Approach to the Synthesis of Enantiomerically Pure Hydroxylated α-Amino Acids Using Zinc Homoenolate Chemistry

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Abstract
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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