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Pentamethylcyclopentadienyl–Ruthenium Catalysts for Regio- and Enantioselective Allylation of Nucleophiles

✍ Scribed by Christian Bruneau; Jean-Luc Renaud; Bernard Demerseman

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 374 KB
Volume: 12
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.200600173

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✦ Synopsis

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.

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## Abstract The simplicity and availability of the nucleophile, the mild conditions, and the broad scope of the allylic chlorides are features of the present reaction.