α-N-HYDROXYAMINO ACID DERIVATIVES

Article abstract of DOI:10.1016/S0040-4020(01)86049-X

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.