Open AccessL-proline/cholesterol and diosgenin based thiourea cooperative system for the direct asymmetric aldol reaction in the presence of water
Author(s) -
Serkan Eymür,
Enis Taşcı,
Arzu Uyanık,
Mustafa Yılmaz
Publication year - 2020
Publication title -
turkish journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.239
H-Index - 46
eISSN - 1303-6130
pISSN - 1300-0527
DOI - 10.3906/kim-2003-36
Subject(s) - chemistry , thiourea , diosgenin , aldol reaction , proline , reactivity (psychology) , selectivity , enantiomer , urea , catalysis , organic chemistry , aromatization , biochemistry , amino acid , medicine , alternative medicine , pathology
A series of cholesterol and based hydrophobic urea and thiourea compounds were synthesized and successfully used as a cocatalyst for L-proline catalyzed aldol reactions in the presence of water. The anticonfigured products were obtained with good yields (up to 94%), high diastereoselectivities (up to 95:5), and high enantiomeric excesses (up to 93% ee ). The successful results for catalytic efficiency of L-proline in the presence of water reveal the importance of the hydrophobic nature of cholesterol and diosgenin parts of thiourea on the reactivity and selectivity in the presence of water.