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Pentamethylcyclopentadienyl–Ruthenium Catalysts for Regio‐ and Enantioselective Allylation of Nucleophiles
Author(s) -
Bruneau Christian,
Renaud JeanLuc,
Demerseman Bernard
Publication year - 2006
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.200600173
Subject(s) - nucleophile , ruthenium , enantioselective synthesis , allylic rearrangement , chemistry , cationic polymerization , regioselectivity , catalysis , combinatorial chemistry , ligand (biochemistry) , medicinal chemistry , organic chemistry , biochemistry , receptor
Abstract Ruthenium( II ) complexes containing the pentamethylcyclopentadienyl ligand efficiently perform the activation of allylic carbonates and halides to generate cationic and dicationic ruthenium( IV ) complexes. This activation has been transferred as a key step to the catalytic allylation of nucleophiles. The structural and electronic properties of the allylic moieties lead to the regioselective formation of chiral products resulting from nucleophilic addition to their most substituted terminus. The catalytic activity of various Ru(Cp*) precatalysts in several allylic substitutions by C and O nucleophiles will be presented. The enantioselective version that has been demonstrated by using optically pure bisoxazoline ligands will also be discussed.