Hidden Heptacyclic Chiral N-Acyl Iminium Ions: a New Entry to Enantioenriched Polycyclic Azepanes and Azocanes by Superacid-Promoted Intramolecular Pictet-Spengler Reaction

Autor: Yasmin Reviriot, Bastien Michelet, Rodolphe Beaud, Agnès Martin‐Mingot, Frédéric Guégan, Sébastien Thibaudeau, Jean Rodriguez, Damien Bonne

Publikováno v: Chemistry-A European Journal
Chemistry-A European Journal, 2022, 28 (25), pp.e202200432. ⟨10.1002/chem.202200432⟩

International audience; Enantioenriched complex fused-tricyclic azepanes or bridged-polycyclic azocanes were constructed via a two-step sequence involving an enantioselective organocascade followed by superacid activation of the domino adduct. The ac

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7c6f5fe8270814f9e11af1f7986e101a
https://hal.science/hal-03769652/document

Enantioenriched Methylene‐Bridged Benzazocanes Synthesis by Organocatalytic and Superacid Activations

Autor: Damien Bonne, Jean Rodriguez, Bastien Michelet, Sébastien Thibaudeau, Yasmin Reviriot, Rodolphe Beaud, Agnès Martin-Mingot

Publikováno v: Angewandte Chemie International Edition
Angewandte Chemie International Edition, Wiley-VCH Verlag, 2020, 59 (3), pp.1279-1285. ⟨10.1002/anie.201912043⟩
Angewandte Chemie International Edition, 2020, 59 (3), pp.1279-1285. ⟨10.1002/anie.201912043⟩

International audience; Achieving in a straightforward way the synthesis of enantioenriched elaborated three-dimensional molecules related to bioactive natural products remains a long-standing quest in organic synthesis. Enantioselective organocataly

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::f787a99aba8bdfff8d12c62eda2d545b
https://hal.archives-ouvertes.fr/hal-03007716

Triflic Acid as an Efficient Brønsted Acid Promoter for the Umpolung of N-Ac Indoles in Hydroarylation Reactions

Autor: Rodolphe Beaud, Didier Gori, Cyrille Kouklovsky, Régis Guillot, Raj Kumar Nandi, Guillaume Vincent, Alejandro Perez-Luna, Vincent Gandon

Publikováno v: Advanced Synthesis and Catalysis
Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2018, 360 (1), pp.161-172. ⟨10.1002/adsc.201701074⟩

We report that triflic acid, a strong Bronsted acid, is a very powerful alternative to FeCl3 to mediate the hydroarylation of N-Ac indoles, which delivers regioselectively 3-arylindolines, 3,3-spiroindolines or 2-arylindolines. Mechanistic exploratio

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1b91697897240c9678958608b58cb5c6
https://doi.org/10.1002/adsc.201701074

The Quest for an Oxidative Coupling of Phenols and Indoles towards Benzofuroindolines: A Two-Stage Approach

Autor: Cyrille Kouklovsky, Annie Pouilhes, Terry Tomakinian, Guillaume Vincent, Rodolphe Beaud, Natacha Denizot

Publikováno v: Synlett. 26:432-440

The benzofuroindoline motif is found in several natural products and its biosynthesis is believed to be the oxidative coupling of phenols and indoles. A two-stage sequence has been developed to assemble these two units through the generation of elect

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::d51d4f49305129e4d7e667eb23093d2d
https://doi.org/10.1055/s-0034-1379495

Revealing the electrophilicity of N-Ac indoles with FeCl _\textrm3 : a mechanistic study

Autor: Raj Kumar Nandi, Rodolphe Beaud, Didier Gori, Cyrille Kouklovsky, Nour-Eddine Ghermani, Vincent Gandon, Régis Guillot, Guillaume Vincent, Alejandro Perez-Luna

Publikováno v: Chemical Communications
Chemical Communications, Royal Society of Chemistry, 2017, 53 (43), pp.5834--5837. ⟨10.1039/C7CC02756G⟩
Chemical Communications, 2017, 53 (43), pp.5834--5837. ⟨10.1039/C7CC02756G⟩

International audience; Herein, we report a mechanistic exploration of the unusual FeCl3-mediated hydroarylation of N-Ac indoles. Electron density topology analysis of a crystal, in situ IR monitoring, Hammett and Taft studies as well as DFT computat

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1021de1cf406dcffc6c76467277b38a6
https://hal.archives-ouvertes.fr/hal-01712357