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

页码：2390 / 2399

页数：10

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