Enantioselective approach to indolizidine and quinolizidine scaffolds. Application to the synthesis of peptide mimics

Yuanyuan Lu, Sílvia Alujas-Burgos, Cristina Oliveras-González, Laura Vázquez-Jiménez, Pep Rojo, Ángel Álvarez-Larena, Pau Bayón, Marta Figueredo

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Abstract

© 2017 Elsevier Ltd An enantioselective approach to substituted indolizidine and quinolizidine frameworks has been developed. Key steps of the synthesis are the enantioselective, palladium-catalyzed N-allylation of an imide, the nucleophilic allylation of an acyliminium ion and a ring closing metathesis. This general strategy has been applied to the synthesis of indolizidine peptide mimics, starting from a chiral imide derived from L-aspartic acid. It was observed that the preexisting stereogenic center of this substrate has a moderate influence on the stereoselectivity of the electrophilic allylation, which is mainly determined by the sense of chirality of the catalyst.
Original languageEnglish
Pages (from-to)104-116
JournalTetrahedron
Volume74
Issue number1
DOIs
Publication statusPublished - 4 Jan 2018

Keywords

  • Indolizidines
  • Peptide mimics
  • Quinolizidines
  • Steroselective synthesis

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    Lu, Y., Alujas-Burgos, S., Oliveras-González, C., Vázquez-Jiménez, L., Rojo, P., Álvarez-Larena, Á., Bayón, P., & Figueredo, M. (2018). Enantioselective approach to indolizidine and quinolizidine scaffolds. Application to the synthesis of peptide mimics. Tetrahedron, 74(1), 104-116. https://doi.org/10.1016/j.tet.2017.11.042