Enantioselective Hydrogenation of Allylphthalimides

Significance

While hydrogenation is one of the most powerful catalytic asymmetric transformations, its application to the synthesis of β-methyl chiral amines was yet to be realized. This paper describes the use of allylphthalimides for the hydrogenation and cleavage of the protecting group (N₂H₄×H₂O/EtOH) to produce chiral amines in high yield and with high enantioselectivity. The use of (S)-C₃-tunephos (L*) as the ligand provided the best results for a number of substrates.