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Creating Chemical Diversity in Indole Compounds by Merging Au and Ru Catalysis
Author(s) -
Bandini Marco,
Eichholzer Astrid,
Gualandi Andrea,
Quinto Tommaso,
Savoia Diego
Publication year - 2010
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201000077
Subject(s) - indole test , tsuji–trost reaction , intramolecular force , catalysis , alkylation , ring closing metathesis , chemistry , metathesis , combinatorial chemistry , ring (chemistry) , allylic rearrangement , organic chemistry , polymerization , polymer
Sequential dual‐metal catalyzed reactions are successfully applied to create chemical diversity in indole polycyclic alkaloids. Gold‐catalyzed intramolecular allylic alkylation of indoles with alcohols, followed by Ru‐assisted ring‐closing metathesis opens up access to a large variety of functionalized tetrahydrocarbazoles and tetrahydro‐β‐carbolines in a straightforward manner. The gold‐catalyzed alkylation allows complex molecular architectures to be realized in a highly regio‐ and stereocontrolled manner.