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Facile Reduction of β-Enamino Oxopyrrolidine Carboxylates Mediated by Heterogeneous Palladium Catalyst

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Abstract

The synthesis of diastereoisomers via diastereoselective hydrogenation of unreactive endocyclic enamine system of ethyl 4-hydrazinyl- and 4-(2-hydroxyethylamino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylates using palladium-based catalyst was developed. The steric and electronic properties of substituents, especially of the C2 substituent, influenced both the yield and diastereoselectivity. Despite the reaction generated three chiral centers, the reduced compounds had either cis–trans or all-trans configuration which was successfully determined by means of 1D and 2D NMR experiments.

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ACKNOWLEDGMENTS

The authors thank Universiti Teknologi MARA and Ministry of Higher Education for the support and members of Organic Synthesis Research Laboratory, I.O.S., UiTM for helpful discussions.

Funding

This study was performed under financial support by the Ministry of Higher Education of Malaysia [600-IRMI/FRGS 5/3 (398/2019)].

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Authors and Affiliations

  1. Faculty of Applied Sciences, Universiti Teknologi MARA, 40450, Shah Alam, Selangor, Malaysia

    F. N. A. Abdul Rashid & F. E. Bouchamma

  2. Organic Synthesis Research Laboratory, Institute of Science, Universiti Teknologi MARA, 42300, Bandar Puncak Alam, Selangor, Malaysia

    M. F. Mohammat, Z. Shaameri & A. S. Hamzah

Authors
  1. F. N. A. Abdul Rashid
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  2. M. F. Mohammat
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  3. F. E. Bouchamma
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  4. Z. Shaameri
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  5. A. S. Hamzah
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Corresponding author

Correspondence to M. F. Mohammat.

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Rashid, F.N.A.A., Mohammat, M.F., Bouchamma, F.E. et al. Facile Reduction of β-Enamino Oxopyrrolidine Carboxylates Mediated by Heterogeneous Palladium Catalyst. Russ J Org Chem 56, 1082–1088 (2020). https://doi.org/10.1134/S1070428020060184

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  • DOI: https://doi.org/10.1134/S1070428020060184

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