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Sydnone-Based Approach to Heterohelicenes through 1,3-Dipolar-Cycloadditions.
Yen-Pon, Expédite; Champagne, Pier Alexandre; Plougastel, Lucie; Gabillet, Sandra; Thuéry, Pierre; Johnson, Mizuki; Muller, Gilles; Pieters, Grégory; Taran, Frédéric; Houk, K N; Audisio, Davide.
Affiliation
  • Yen-Pon E; Service de Chimie Bio-organique et Marquage (SCBM), JOLIOT , CEA, Université Paris-Saclay , 91191 Gif-sur-Yvette , France.
  • Champagne PA; Department of Chemistry and Biochemistry , University of California , Los Angeles , California 90095 , United States.
  • Plougastel L; Service de Chimie Bio-organique et Marquage (SCBM), JOLIOT , CEA, Université Paris-Saclay , 91191 Gif-sur-Yvette , France.
  • Gabillet S; Service de Chimie Bio-organique et Marquage (SCBM), JOLIOT , CEA, Université Paris-Saclay , 91191 Gif-sur-Yvette , France.
  • Thuéry P; NIMBE, CEA, CNRS, Université Paris-Saclay , 91191 Gif-sur-Yvette , France.
  • Johnson M; Department of Chemistry , San José State University , San José , California 95192-0101 , United States.
  • Muller G; Department of Chemistry , San José State University , San José , California 95192-0101 , United States.
  • Pieters G; Service de Chimie Bio-organique et Marquage (SCBM), JOLIOT , CEA, Université Paris-Saclay , 91191 Gif-sur-Yvette , France.
  • Taran F; Service de Chimie Bio-organique et Marquage (SCBM), JOLIOT , CEA, Université Paris-Saclay , 91191 Gif-sur-Yvette , France.
  • Houk KN; Department of Chemistry and Biochemistry , University of California , Los Angeles , California 90095 , United States.
  • Audisio D; Service de Chimie Bio-organique et Marquage (SCBM), JOLIOT , CEA, Université Paris-Saclay , 91191 Gif-sur-Yvette , France.
J Am Chem Soc ; 141(4): 1435-1440, 2019 01 30.
Article in En | MEDLINE | ID: mdl-30628450
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.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Polycyclic Compounds / Sydnones / Cycloaddition Reaction Language: En Journal: J Am Chem Soc Year: 2019 Document type: Article Affiliation country: France Country of publication: United States
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Polycyclic Compounds / Sydnones / Cycloaddition Reaction Language: En Journal: J Am Chem Soc Year: 2019 Document type: Article Affiliation country: France Country of publication: United States