Efficient asymmetric synthesis of amino acids through hydrogenation of the didehydroamino acid residue in cyclic imino-ester derivatives

Article abstract of DOI:10.1016/S0957-4166(00)80263-3

The trisubstituted olefinic bond of chiral cyclic α,β-didehydroamino acid derivatives was hydrogenated in the presence of Pd/C with >95% diastereoface discrimination to give, after hydrolysis, the corresponding S-amino acids. The reduction of the double bond with L-selectride does not change the orientation of diastereoface discrimination and the diastereoselectivity is still high.