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Noscapine-derived β-amino alcohols as new organocatalysts for enantioselective addition of diethylzinc to aldehydes

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Abstract

In this paper, synthesis of two derivatives of noscapine and their application as organocatalysts in the asymmetric addition of diethylzinc to aromatic aldehydes is reported. The first catalyst (2) was synthesized by the reduction of lactone ring of noscapine to form the corresponding diol, and the second one (3) was prepared by tert-butyl dimethyl silylation of the primary hydroxyl group of 2. Excellent yields and high ees up to 95% were obtained by using 3 as the catalyst. To the best of our knowledge, this is the first report on the application of lactone ring opened noscapinoid compounds as organocatalysts in asymmetric reactions.

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Acknowledgements

The authors would like to thank the Iran National Science Foundation (INSF, Grant Number 94-S-43569) for financial support of the work and Shahid Beheshti University Research Council for the facilitation of the process to conduct this study.

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Authors and Affiliations

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

    Maryam Mohebbi, Peyman Salehi, Morteza Bararjanian & Samad N. Ebrahimi

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  1. Maryam Mohebbi
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  2. Peyman Salehi
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  3. Morteza Bararjanian
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  4. Samad N. Ebrahimi
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Correspondence to Peyman Salehi.

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Mohebbi, M., Salehi, P., Bararjanian, M. et al. Noscapine-derived β-amino alcohols as new organocatalysts for enantioselective addition of diethylzinc to aldehydes. J IRAN CHEM SOC 15, 47–53 (2018). https://doi.org/10.1007/s13738-017-1207-9

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