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New organocatalysts derived from tetrahydropapaverine for asymmetric aldol reaction

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Abstract

Abstract

Synthesis of prolinamide derivatives of (R)-tetrahydropapaverine as mono-, di- and tripeptide is reported. (R)-Tetrahydropapaverine-prolinamide hybrid derivatives were tested as organocatalysts in the asymmetric Aldol reaction of aldehydes and ketones within various solvents, temperatures, and molar ratios. Catalyst 2 (30 mol %) afforded the best result in the Aldol reaction of cyclohexanone with 4-nitrobenzaldehyde up to 90% ee. Although in the sole presence of l-proline the reaction proceeded with anti-stereoselectivity, its hybridization with (R)-tetrahydropapaverine yielded the formation of syn products as the major compounds.

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Acknowledgements

We are thankful to Shahid Beheshti University Research Council for partial support of this work. Also cooperation of Tofigh Daru Research and Engineering Company in this project is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, 1983963113, Tehran, Iran

    Sedigheh Sadat Naeimi, Peyman Salehi & Morteza Bararjanian

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  1. Sedigheh Sadat Naeimi
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  2. Peyman Salehi
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  3. Morteza Bararjanian
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Correspondence to Peyman Salehi.

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Naeimi, S.S., Salehi, P. & Bararjanian, M. New organocatalysts derived from tetrahydropapaverine for asymmetric aldol reaction. J IRAN CHEM SOC 19, 3407–3416 (2022). https://doi.org/10.1007/s13738-022-02535-6

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