Open AccessSynthesis of New Di- and Triamides as Potential Organocatalysts for Asymmetric Aldol Reaction in Water
Author(s) -
Elif Keskin,
Çiğdem Yolaçan,
Feray Aydoğan
Publication year - 2020
Publication title -
acta chimica slovenica
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.289
H-Index - 46
eISSN - 1580-3155
pISSN - 1318-0207
DOI - 10.17344/acsi.2018.4748
Subject(s) - aldol reaction , chemistry , benzoic acid , pyrrolidine , organocatalysis , proline , catalysis , organic chemistry , reaction conditions , enantioselective synthesis , amino acid , biochemistry
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 °C in the presence of benzoic acid as co-catalyst. (S)-methyl-2-((S)-3-hydroxy-2-((S)-3-pyrrolidine-2-carboxamido)propanamido)-3-phenylpropanoate (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.