Sydnone-Based Approach to Heterohelicenes through 1,3-Dipolar-Cycloadditions

Expédite Yen-Pon, Pier Alexandre Champagne, Lucie Plougastel, Sandra Gabillet, Pierre Thuéry, Mizuki Johnson, Gilles Muller, Grégory Pieters, Frédéric Taran, K. N. Houk, Davide Audisio

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

The first approach to pyrazole-containing helicenes via sydnone-aryne [3 + 2]-cycloaddition is described. An unprecedented regioselectivity in the cycloaddition step toward the more sterically constrained product was observed in the presence of extended aromatic scaffolds. DFT calculations enabled understanding the origin of this unexpected selectivity.

Original languageEnglish (US)
Pages (from-to)1435-1440
Number of pages6
JournalJournal of the American Chemical Society
Volume141
Issue number4
DOIs
StatePublished - Jan 30 2019
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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