Premium
Merging Organocatalysis and Gold Catalysis: Enantioselective Synthesis of Tetracyclic Indole Derivatives through a Sequential Double Friedel–Crafts Type Reaction
Author(s) -
Loh Charles C. J.,
Badorrek Jan,
Raabe Gerhard,
Enders Dieter
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201102793
Subject(s) - indole test , friedel–crafts reaction , organocatalysis , enantioselective synthesis , chemistry , catalysis , combinatorial chemistry , organic chemistry , stereochemistry
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.