New expedient route to both enantiomers of nonproteinogenic α-amino acid derivatives from the unsaturated 2-aza-bicyclo moiety

The influence of the reaction conditions on the catalytic hydrogenation of 2-aza-bicyclo hept-5-ene and oct-5-ene derivatives has been investigated. We found it possible to fully control the extent of allylic vs benzylic C-N hydrogenolysis by simple variations of H-2 pressure and acidity of the reaction medium. The use of the reaction pathways was demonstrated by the selective preparation of four categories of optically active alpha-amino acid derivatives. The strategy was also extended to the synthesis of enantiopure alpha-amino ketones.