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Highly Diastereoselective Metal-Free Catalytic Synthesis of Drug-Like Spiroimidazolidinone

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Abstract

A four-step procedure has been developed for the synthesis of (S)-3-isopropyl-1-[(R)-1-phenylethyl)- 1,4-diazaspiro[4.5]decan-2-one with high diastereoselectivity (up to 95% de) from (S)-α-aminoisovaleric acid (L-valine). Quantum chemical computations of the synthesized compound have been performed using Gaussian 09 software package.

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Acknowledgments

The authors gratefully acknowledge Sheffield University (UK) for recording IR, 1H and 13C NMR, and high-resolution mass spectra.

Funding

This work was financially supported by the Ministry of Higher Education and Scientific Research (Iraq).

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Authors and Affiliations

  1. Department of Chemistry, College of Education for Pure Sciences, Basrah University, Basrah, Iraq

    A. M. Jassem & H. A. Jaber

  2. Department of Chemistry, College of Science, Al-Mustansiriya University, Baghdad, Iraq

    A. H. Raheemah

  3. Department of Chemistry, Polymer Research Center, Basrah University, Basrah, Iraq

    W. A. Radhi

  4. Department of Material Science, Polymer Research Center, Basrah University, Basrah, Iraq

    A. M. Alid

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  1. A. M. Jassem
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  2. A. H. Raheemah
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  3. W. A. Radhi
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  4. A. M. Alid
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Correspondence to A. M. Jassem.

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Jassem, A.M., Raheemah, A.H., Radhi, W.A. et al. Highly Diastereoselective Metal-Free Catalytic Synthesis of Drug-Like Spiroimidazolidinone. Russ J Org Chem 55, 1598–1603 (2019). https://doi.org/10.1134/S107042801910021X

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  • DOI: https://doi.org/10.1134/S107042801910021X

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