Sequential Photochemical and Prins Reactions for the Diastereoselective Synthesis of Tricyclic Scaffolds

Bethan Donnelly, Luke Elliott, Chris Willis, Kevin Booker-Milburn*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

12 Citations (Scopus)
67 Downloads (Pure)

Abstract

Cyclobutene alcohols undergo Prins cyclisations to generate single diastereomers of novel tricyclic heterocycles with five contiguous stereocentres. The reaction times are significantly shorter (ca. 15 min) than with traditional alkene substrates. Stereoselective aza-Prins cyclisations of cyclobutene amine derivatives give fused aza-heterocyclic scaffolds. Computational studies provide insight into the observed stereocontrol. The modular approach is flexible, enabling the introduction of a variety of functional groups (including amides, nitriles, alkynes, and arenes) into the sp3-rich heterocyclic scaffolds.

Original languageEnglish
Pages (from-to)9095-9098
Number of pages4
JournalAngewandte Chemie - International Edition
Volume58
Issue number27
Early online date24 May 2019
DOIs
Publication statusPublished - 24 Jun 2019

Structured keywords

  • BCS and TECS CDTs

Keywords

  • cyclobutene
  • flourination
  • photochemistry
  • Prins cyclisation
  • ritter reaction

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