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Novel and highly efficient bifunctional calixarene thiourea derivatives as organocatalysts for enantioselective Michael reaction of nitroolefins with diketones

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Abstract

New bifunctional calixarene thiourea organocatalysts were synthesized and applied in catalytic asymmetric Michael addition of acetylacetone to various nitroolefins at room temperature. The corresponding adducts were obtained in good to excellent yields with excellent enantioselectivities (up to 92% ee). The present research demonstrates the advantages of incorporating two stereocontrolling structures into a single catalyst. Notably, it offers a simple and convenient doubly stereocontrolled approach for the catalytic asymmetric synthesis of a chiral organic molecule.

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Acknowledgements

The authors gratefully acknowledge the financial support of this work given by the Scientific and Technological Research Council of Turkey (TUBITAK-113Z696) and Research Foundation of Necmettin Erbakan University (BAP-141110003).

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  1. Department of Chemistry, Necmettin Erbakan University, 42090, Konya, Turkey

    Hayriye Nevin Genc & Abdulkadir Sirit

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  1. Hayriye Nevin Genc
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  2. Abdulkadir Sirit
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Correspondence to Abdulkadir Sirit.

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Genc, H.N., Sirit, A. Novel and highly efficient bifunctional calixarene thiourea derivatives as organocatalysts for enantioselective Michael reaction of nitroolefins with diketones. J Incl Phenom Macrocycl Chem 90, 39–49 (2018). https://doi.org/10.1007/s10847-017-0761-1

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