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Design and Catalytic Asymmetric Synthesis of Furan‐Indole Compounds Bearing both Axial and Central Chirality
Ist Teil von
Angewandte Chemie International Edition, 2024-02, Vol.63 (8), p.e202316454-n/a
Auflage
International ed. in English
Ort / Verlag
Germany: Wiley Subscription Services, Inc
Erscheinungsjahr
2024
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
In the chemistry community, catalytic asymmetric synthesis of furan‐based compounds bearing both axial and central chirality has proven to be a significant but challenging issue owing to the importance and difficulty in constructing such frameworks. In this work, we have realized the first catalytic asymmetric synthesis of five‐five‐membered furan‐based compounds bearing both axial and central chirality via organocatalytic asymmetric (2+4) annulation of achiral furan‐indoles with 2,3‐indolyldimethanols with uncommon regioselectivity. By this strategy, furan‐indole compounds bearing both axial and central chirality were synthesized in high yields with excellent regio‐, diastereo‐, and enantioselectivities. Moreover, theoretical calculations were conducted to provide an in‐depth understanding of the reaction pathway, activation mode, and the origin of the selectivity.
The first catalytic asymmetric synthesis of five‐five‐membered furan‐based compounds bearing both axial and central chirality has been established via organocatalytic asymmetric (2+4) annulation with uncommon regioselectivity in high yields with excellent regio‐, diastereo‐, and enantioselectivities. Theoretical calculations provide an in‐depth understanding of the reaction pathway and the origin of selectivity.