α-n-hydroxyamino acid derivatives

Reactions of organolithium reagents with glyoxylate derived oximes provided a direct route to α-N-hydroxyamino acids. The process required direct attachment of an ionizable group to the glyoxylate carbonyl to prevent competitive reactions. The procedure allowed for direct formation of the α-chiral center of the newly formed α-N-hydroxyamino acid derivative. Introduction of potential chiral auxiliaries on the oxime oxygen resulted in modest diastereoselection. In most instances, use of chiral glyoxylamides also gave low diastereoselectivity.