Merging Organocatalysis and Gold Catalysis: Enantioselective Synthesis of Tetracyclic Indole Derivatives through a Sequential Double Friedel-Crafts Type Reaction

Yet another indole miracle: The sequential combination of organocatalysis and gold catalysis on C2,C3‐unsubstituted indoles provides an efficient one‐pot access to tetracyclic indole derivatives in very good yields and excellent enantioselectivities (see scheme). The double Friedel–Crafts type react...

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Veröffentlicht in:Chemistry : a European journal 2011-11, Vol.17 (48), p.13409-13414
Hauptverfasser: Loh, Charles C. J., Badorrek, Jan, Raabe, Gerhard, Enders, Dieter
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Sprache:eng
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Zusammenfassung:Yet another indole miracle: The sequential combination of organocatalysis and gold catalysis on C2,C3‐unsubstituted indoles provides an efficient one‐pot access to tetracyclic indole derivatives in very good yields and excellent enantioselectivities (see scheme). The double Friedel–Crafts type reaction, including a rare 7‐endo‐dig cyclisation, opens a new entry to highly enantioenriched anticancer drugs, such as DNA intercalators.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201102793