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Thieme Gruppe, Synthesis: Journal of Synthetic Organic Chemistry, 04(54), p. 1101-1107, 2021

DOI: 10.1055/s-0040-1719858

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An Approach to the Synthesis of a Hepatitis C Virus Inhibitor through a Proline-Catalyzed 1,3-Dipolar Cycloaddition Using Acrolein

Journal article published in 2021 by Luisa Carrillo, Jose L. Vicario ORCID, Iratxe Ugarriza, Efraím Reyes ORCID, Liher Prieto ORCID, Uxue Uria ORCID
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Abstract

AbstractAn efficient and easy protocol for performing 1,3-dipolar cycloaddition using azomethine ylides and acrolein is presented. The reaction catalyzed by d-proline allows the synthesis of C-3 unsubstituted pyrrolidines. The application of this methodology to the synthesis of an advanced intermediate in the preparation of a Hepatitis C virus inhibitor is presented. Final attempts to complete the synthesis of the target inhibitor results in the preparation of its C-4 epimer in good overall yield.