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

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Abstract

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-diastereoselectivity (anti/syn = 92 : 8) and high enantioselectivity (ee 88%) were obtained from the reaction between cyclohexanone and 4-fluorobenzaldehyde in the presence of water.

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Funding

Financial supports by The Scientific and Technological Research Council of Türkiye (Grant no. TBAG-112T349), and Scientific Research Projects Foundation of Selcuk University (SUBAP) are acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Selçuk University, 42130, Konya, Turkey

    A. Uyanik, O. Sahin, E. Akceylan & M. Yilmaz

  2. Department of Energy Systems Engineering, Faculty of Engineering, Giresun University, 28200, Giresun, Turkey

    S. Eymur

  3. Department of Metallurgical and Materials Engineering, Faculty of Technology, Selçuk University, 42130, Konya, Turkey

    I. Uyanik

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  1. A. Uyanik
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  2. O. Sahin
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  3. E. Akceylan
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Uyanik, A., Sahin, O., Akceylan, E. et al. Effect of Calix[4]arene as a Hydrophobic Substituent on Proline Catalysis of Direct Asymmetric Aldol Reactions in the Presence of Water. Russ J Gen Chem 92, 2390–2399 (2022). https://doi.org/10.1134/S107036322211024X

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