L-threo- and L-erythro-3-Fluoroglutamic Acids. Synthesis by Fluorodehydroxylation and Enzymatic Resolution.

Article abstract of DOI:10.1021/jo00217a029

threo- and erythro-3-fluoroglutamic acids were prepared by fluorodehydroxylation of N-acetyl-3-hydroxyglutamic acids according to Kollonitsch.Following ion exchange column separation of the diastereoisomers, enzymatic deacylation by acylase I afforded optically pure L-isomers of the 3-fluoroglutamic acid.Assignment of structure was achieved by correlation with cis- and trans-3-fluoropyroglutamic acids.The results indicate predominant inversion of configuration during the fluorodehydroxylation reaction.