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Enantioselective Gold‐Catalyzed Allylic Alkylation of Indoles with Alcohols: An Efficient Route to Functionalized Tetrahydrocarbazoles
Author(s) -
Bandini Marco,
Eichholzer Astrid
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200904388
Subject(s) - enantioselective synthesis , tsuji–trost reaction , intramolecular force , friedel–crafts reaction , catalysis , alkylation , allylic rearrangement , taboo , chemistry , combinatorial chemistry , organic chemistry , political science , law
Breaking the taboo : The direct use of allylic alcohols in catalytic and enantioselective Friedel–Crafts alkylation is described for the first time in the presence of chiral gold complexes. This intramolecular Friedel–Crafts reaction was used to prepare a broad range of functionalized tetrahydrocarbazoles (see scheme; X=Me, F, Br, Cl, OMe; R=Me, Et, t Bu; R′=H, Me).