4.8 Article

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

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 4, Pages 1435-1440

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b11465

Keywords

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Funding

  1. CEA [ANR-17-CE07-0035-01]
  2. ANR [ANR-17-CE07-0035-01]
  3. U.S. National Science Foundation [CHE-1361104]
  4. Fonds de recherche du Quebec Nature et Technologies
  5. NIH Minority Biomedical Research Support [1 SC3 GM089589-08]
  6. Henry Dreyfus Teacher -Scholar Award

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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 under-standing the origin of this unexpected selectivity.

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