General acid-mediated aminolactone formation using unactivated alkenes

David Just, Carlos R. Gonçalves, Uroš Vezonik, Daniel Kaiser, Nuno Maulide (Corresponding author)

Publications: Contribution to journalArticlePeer Reviewed

Abstract

Spirocyclic butyrolactones and butenolides are widespread structural motifs in bioactive substances. Despite their prevalence, a simple method ensuring their direct preparation from exocyclic alkenes, ideally in a late-stage context, remains elusive. Herein, we report direct aminolactone formation using unactivated alkenes which addresses this gap, employing cheap and readily available reactants. The method relies on the hijacking of a cationic aminoalkylation pathway and affords (spiro)aminolactones with excellent functional group tolerance and chemoselectivity. The synthetic versatility of the products is demonstrated through a range of transformations, notably exploiting stereospecific rearrangement chemistry to produce sterically congested scaffolds.

Original languageEnglish
Pages (from-to)10806-10811
Number of pages6
JournalChemical Science
Volume14
Issue number39
DOIs
Publication statusPublished - 28 Sep 2023

Austrian Fields of Science 2012

  • 104015 Organic chemistry

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