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

被引:2
作者
Eymur, Serkan [1 ]
Tasci, Enis [2 ]
Uyanik, Arzu [3 ]
Yilmaz, Mustafa [3 ]
机构
[1] Giresun Univ, Fac Engn, Dept Energy Syst Engn, Giresun, Turkey
[2] Giresun Univ, Vocat Sch Hlth Serv, Giresun, Turkey
[3] Selcuk Univ, Fac Sci, Dept Chem, Konya, Turkey
关键词
Aldol; organocatalyst; proline; asymmetric synthesis; L-PROLINE; ORGANOCATALYST; ADDITIVES; KETONES; MEDIA;
D O I
10.3906/kim-2003-36
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:1278 / +
页数:28
相关论文
共 39 条
[1]   Primary amine catalyzed direct asymmetric aldol reaction assisted by water [J].
Amedjkouh, M .
TETRAHEDRON-ASYMMETRY, 2005, 16 (08) :1411-1414
[2]   Asymmetric Supramolecular Organocatalysis: A Complementary Upgrade to Organocatalysis [J].
Anebouselvy, Kengadarane ;
Shruthi, Kodambahalli S. ;
Ramachary, Dhevalapally B. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (37) :5460-5483
[3]   Water: the most versatile and nature's friendly media in asymmetric organocatalyzed direct aldol reactions [J].
Bhowmick, Sudipto ;
Mondal, Anirban ;
Ghosh, Ayndrila ;
Bhowmick, Kartick C. .
TETRAHEDRON-ASYMMETRY, 2015, 26 (21-22) :1215-1244
[4]   Catalytic asymmetric carbon-carbon bond-forming reactions in aqueous media [J].
Bhowmick, Sudipto ;
Bhowmick, Kartick C. .
TETRAHEDRON-ASYMMETRY, 2011, 22 (23) :1945-1979
[5]   Proline-based dipeptides with two amide units as organocatalyst for the asymmetric aldol reaction of cyclohexanone with aldehydes [J].
Chen, Fubin ;
Huang, Shi ;
Zhang, Hui ;
Liu, Fengying ;
Peng, Yungui .
TETRAHEDRON, 2008, 64 (40) :9585-9591
[6]   Direct asymmetric aldol reaction co-catalyzed by L-proline and isothiouronium salts [J].
Cho, Eun ;
Kim, Taek Hyeon .
TETRAHEDRON LETTERS, 2014, 55 (47) :6470-6473
[7]   Highly Enantio- and Diastereoselective Organocatalytic Desymmetrization of Prochiral Cyclohexanones by Simple Direct Aldol Reaction Catalyzed by Proline [J].
Companyo, Xavier ;
Valero, Guillem ;
Crovetto, Luis ;
Moyano, Albert ;
Rios, Ramon .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (27) :6564-6568
[8]   Short α/β-peptides as catalysts for intra- and intermolecular aldol reactions [J].
D'Elia, Valerio ;
Zwicknagl, Hans ;
Reiser, Oliver .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (08) :3262-3265
[9]   Self-assembly of an organocatalyst for the enantioselective synthesis of Michael adducts and α-aminoxy alcohols in a nonpolar medium [J].
Demir, Ayhan Sitki ;
Basceken, Sinan .
TETRAHEDRON-ASYMMETRY, 2013, 24 (19) :1218-1224
[10]   Synthesis of a bipyridine-derived achiral thiourea trifluoromethanesulfonic acid salt and its application as an additive in organocatalytic asymmetric reactions [J].
Demir, Ayhan Sitki ;
Basceken, Sinan .
TETRAHEDRON LETTERS, 2013, 54 (42) :5677-5681