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Highly diastereoselective C → N acyl rearrangement in polysubstituted pyrrolidine 2,2-dicarboxylates. Stereocontrolled synthesis of densely functionalized prolines

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Abstract

An efficient and easy protocol for promoting a C → N acyl transfer reaction in diverse enantiopure densely substituted pyrrolidine 2,2-dicarboxylates was performed, yielding the corresponding proline ester derivatives with yields in the range of 68–99% and total diastereoselection (dr > 95 : 5 in all cases). The substitution patterns both at C-3 and C-5 present in starting pyrrolidines as well as the viability of presenting different alkoxycarbonyl moieties have been evaluated observing good reaction performance in all cases.

Graphical abstract: Highly diastereoselective C → N acyl rearrangement in polysubstituted pyrrolidine 2,2-dicarboxylates. Stereocontrolled synthesis of densely functionalized prolines

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Publication details

The article was received on 04 Sep 2017, accepted on 05 Dec 2017 and first published on 12 Dec 2017


Article type: Research Article
DOI: 10.1039/C7QO00793K
Citation: Org. Chem. Front., 2018, Advance Article
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    Highly diastereoselective C → N acyl rearrangement in polysubstituted pyrrolidine 2,2-dicarboxylates. Stereocontrolled synthesis of densely functionalized prolines

    S. Reboredo, A. García-Marijuan, U. Uria, E. Reyes, L. Carrillo, I. Ugarriza and J. L. Vicario, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00793K

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