Various kinds of aminocinnamic acid derivatives were hydrogenated with different stereoselectivities. In the presence of cinchonidine or (-)- dihydroapovincaminic acid ethyl ester modifiers, the enantioselective hydrogenations resulted in very low enantiomeric excesses (ee). Moderate diastereomeric excesses (de, 5-68%) were achieved in the diastereoselective hydrogenations. The highest de (68%) was obtained in the hydrogenation of N- acetyldehydrophenylalanyl-(S)-prolinanilide due to a 10-member intermediate stabilized by hydrogen bond.
ASJC Scopus subject areas
- Process Chemistry and Technology
- Physical and Theoretical Chemistry