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One-pot organocatalytic/multicomponent approach for the preparation of novel enantioenriched non-natural selenium-based peptoids and peptide–peptoid conjugates

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Abstract

A combined organocatalytic and multicomponent synthetic approach was designed for the preparation of selenium-based peptoids and peptide–peptoid conjugates. This single-step synthetic protocol comprises the organocatalytic asymmetric insertion of phenylselenium in the aldehyde moiety followed by the Ugi four-component reaction which results in obtaining the desired compounds in good-to-moderate yields and with good-to-excellent levels of stereoselectivity.

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Acknowledgements

A.F. de la Torre is grateful to financial support from CNPq (14/403846) and Fondecyt 3170003. We also gratefully acknowledge financial support from CNPq (INCT-Catálise), CAPES (CAPES-MES/Cuba Program) and FAPESP (14/50249-8 and 15/17141-1). A. Ali is thankful to TWAS-CNPq for the fellowship and support from the higher education commission of Pakistan (Project No. 21-2037/SRGP/R&D/HEC/2018).

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Authors and Affiliations

  1. Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Concepción, Edmundo Larenas 234-interior -Casilla 160-C, Concepción, Chile

    Alexander F. de la Torre

  2. Department of Chemistry, University of Sargodha, Sargodha, 40100, Pakistan

    Akbar Ali

  3. Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, SC, 88040-900, Brazil

    Fábio Z. Galetto & Antonio L. Braga

  4. Center of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos – UFSCar, Rodovia Washington Luís, km 235 - SP-310, São Carlos, São Paulo, 13565-905, Brazil

    Alexander F. de la Torre, José A. C. Delgado & Márcio W. Paixão

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  1. Alexander F. de la Torre
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  2. Akbar Ali
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de la Torre, A.F., Ali, A., Galetto, F.Z. et al. One-pot organocatalytic/multicomponent approach for the preparation of novel enantioenriched non-natural selenium-based peptoids and peptide–peptoid conjugates. Mol Divers 24, 1–10 (2020). https://doi.org/10.1007/s11030-019-09923-w

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