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Abstract
Reaction of molecular fluorine with unsaturated azlactones derived from appropriate aldehydes (or ketones) and benzoylglycine afforded the difluorinated adducts. The reductive amination reaction of the β-fluorinated α-oxoalkanoic acids obtained from the adducts by basic hydrolysis gave erythro-β-fluorinated aliphatic α-amino acids. The same reactions, when applied to methyl 3-phenyl-2-benzoylaminoacrylate, afforded the corresponding aromatic amino acid. Hence, the entire sequence provides a general method for the synthesis of erythro-β-fluorinated α-amino acids.
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