Synthesis of New Di- and Triamides as Potential Organocatalysts for Asymmetric Aldol Reaction in Water

Abstract

New di- or triamide organocatalysts derived from (L)-proline were synthesized and successfully used in the direct asymmetric aldol reaction of aliphatic ketones and aromatic aldehydes in water at 0 degrees C in the presence of benzoic acid as co-catalyst. (S)-methyl-24(S)-3-hydroxy-2-((S)-3-pyrrolidine-2-carb oxamido)prop an amido) -3-phenylprop ano ate (7c) as organocatalyst showed best results under these reaction conditions, and good diastereoselectivities (up to 99%), enantioselectivities (up to 98%) and yields (up to 91%) were observed.