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Efficient, Transition Metal Mediated, Sequential, Two‐ and Three‐Component Coupling Reactions for the Synthesis of Highly Substituted Five‐Membered Ring Carbocycles
Author(s) -
Coia Nicolas,
Bouyssi Didier,
Balme Geneviève
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700197
Subject(s) - transmetalation , chemistry , intramolecular force , ring (chemistry) , component (thermodynamics) , coupling reaction , transition metal , sequence (biology) , combinatorial chemistry , reaction conditions , coupling (piping) , stereochemistry , medicinal chemistry , computational chemistry , organic chemistry , catalysis , mechanical engineering , biochemistry , physics , engineering , thermodynamics
Abstract A Cu‐catalysed method for the preparation of highly substituted methylenecyclopentanes, through a sequence involving a Michael addition of stabilized enolates to activated enynes followed by an intramolecular carbocupration reaction, is presented. This method was also successfully combined with a Pd‐mediated coupling reaction to perform a new three‐component reaction through a transmetallation pathway on the vinylcopper intermediate. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)