:
The aldol reaction which is the most important one among the C-C bond forming reactions, is widely used by
synthetic organic chemists to obtain β-hydroxycarbonyl compounds which are important starting components for biologically
active compounds in optically pure form. In this research, five Pro-Phe derivatives were synthesized by simple amidation
reactions and characterized by their spectral data. Their catalytic activities in asymmetric aldol reaction were investigated.
The catalytic activity studies were performed with aliphatic ketones and various aromatic aldehydes. Especially, (S)-methyl
3-mercapto-2-((S)-3-phenyl-2-((S)-pyrrolidine-2-carboxamido)propanamido)propanoate showed good catalytic activities in
water at 0
oC in the presence of p-nitrobenzoic acid cocatalyst. The enantioselectivities were upto 90.4%, the diastereomeric
ratios were upto 97/3 and yields were 99%. The results showed that these organocatalysts were promising organocatalysts for
aldol reaction. Besides, this catalyst showed its best catalytic activities in water which is also important contribution to green
chemistry requirements.