Regio- and stereocontrolled hydrocyanation of chiral 2-alkylglycidamides with Et2AlCN: synthesis of enantiomerically pure mono- and disubstituted malic acid derivatives

Abstract The opening of the oxirane ring of glycidamides with Et 2 AlCN takes place under mild conditions in a completely regio- and stereoselective manner to afford β-cyano carboxamide derivatives, which are immediate precursors of mono- and disubstituted malic acid derivatives. The complete control of the regioselectivity can be rationalized as a consequence of the association of the reagent with the carboxamide group prior to intramolecular cyanide transfer.