Effect of Calix[4]arene as a Hydrophobic Substituent on Proline Catalysis of Direct Asymmetric Aldol Reactions in the Presence of Water

被引：0
作者：
Uyanik, A. [1 ]
Sahin, O. [1 ]
Akceylan, E. [1 ]
Eymur, S. [2 ]
Uyanik, I. [3 ]
Yilmaz, M. [1 ]
机构：
[1] Selcuk Univ, Fac Sci, Dept Chem, TR-42130 Konya, Turkey
[2] Giresun Univ, Fac Engn, Dept Energy Syst Engn, TR-28200 Giresun, Turkey
[3] Selcuk Univ, Fac Technol, Dept Met & Mat Engn, TR-42130 Konya, Turkey
来源：
RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2022年 / 92卷 / 11期
关键词：
organocatalysis; direct asymmetric aldol reaction; L-proline; calix[4]arene; TRANSITION-STATES; ORGANOCATALYST; STEREOSELECTIVITIES; ALDEHYDES; KETONES; INVOLVEMENT; DERIVATIVES; MECHANISM; MOLECULE; ION;
D O I：
10.1134/S107036322211024X
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new organocatalyst trans-4-hydroxy-L-proline-derived calix[4]arene was synthesized and its catalyst performance for the direct asymmetric aldol reactions between cyclohexanone and different aromatic aldehydes was investigated. The effect of a series of reaction conditions such as solvent, water and additives were evaluated in detail, and it was observed that the addition of water had a big effect on the enantioselectivities. Specifically, high anti-diastereo selectivity (anti/syn = 92 : 8) and high enantioselectivity (ee 88%) were obtained from the reaction between cyclohexanone and 4-fluorobenzaldehyde in the presence of water.
引用
收藏
页码：2390 / 2399
页数：10
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