Chiral Phosphathiahelicenes: Improved Synthetic Approach and Uses in Enantioselective Gold(I)-Catalyzed [2 + 2] Cycloadditions of N -Homoallenyl Tryptamines
| Autor: | Angela Marinetti, Arnaud Voituriez, Xavier Guinchard, Valentin Magné, Youssouf Sanogo, Charles S. Demmer, Pascal Retailleau |
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| Přispěvatelé: | Institut de Chimie des Substances Naturelles (ICSN), Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Phosphorus ligands
Phosphole Sequence (biology) 010402 general chemistry 01 natural sciences Catalysis spirofused compounds helicenes chemistry.chemical_compound Thiophene [CHIM]Chemical Sciences ComputingMilieux_MISCELLANEOUS 010405 organic chemistry Chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Enantioselective synthesis tryptamines Halogenation General Chemistry [CHIM.CATA]Chemical Sciences/Catalysis Combinatorial chemistry Cycloaddition gold catalysis 0104 chemical sciences Tryptamines indolinecyclobutanes |
| Zdroj: | ACS Catalysis ACS Catalysis, American Chemical Society, 2020, 10 (15), pp.8141-8148. ⟨10.1021/acscatal.0c01819⟩ ACS Catalysis, American Chemical Society, 2020, ⟨10.1021/acscatal.0c01819⟩ |
| ISSN: | 2155-5435 |
| Popis: | International audience; A chiral phosphathiahelicene scaffold displaying a phosphole and a thiophene unit as the terminal rings of the helical sequence has been synthesized and characterized by spectroscopic methods and X-ray diffraction studies. The phosphine oxides (HelPhos-V oxides) have been obtained following a robust and scalable synthetic approach, based on a nickel-promoted alkynes cyclotrimerization reaction. Then, late-stage functionalization has been carried out via a bromination/palladium coupling reaction sequence. The HelPhos-V gold(I) complexes have been used as catalysts in the unprecedented enantioselective [2+2] cyclization of N-homoallenyl tryptamine derivatives, to afford indolenine-fused cyclobutanes in good isolated yields, with enantiomeric excesses up to 93%. |
| Databáze: | OpenAIRE |
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