L-proline/cholesterol and diosgenin based thiourea cooperative system for the directasymmetric aldol reaction in the presence of water

Authors

SERKAN EYMUR
ENİS TAŞCI
ARZU UYANIK
MUSTAFA YILMAZ

DOI

10.3906/kim-2003-36

Abstract

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.

Keywords

Aldol, organocatalyst, proline, asymmetric synthesis

First Page

1278

Last Page

1284

Recommended Citation

EYMUR, SERKAN; TAŞCI, ENİS; UYANIK, ARZU; and YILMAZ, MUSTAFA (2020) "L-proline/cholesterol and diosgenin based thiourea cooperative system for the directasymmetric aldol reaction in the presence of water," Turkish Journal of Chemistry: Vol. 44: No. 5, Article 5. https://doi.org/10.3906/kim-2003-36
Available at: https://journals.tubitak.gov.tr/chem/vol44/iss5/5