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Ruthenium Catalysts for Controlled Mono- and Bis-Allylation of Active Methylene Compounds with Aliphatic Allylic Substrates

✍ Scribed by Hui-Jun Zhang; Bernard Demerseman; Zhenfeng Xi; Christian Bruneau

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
165 KB
Volume
351
Category
Article
ISSN
1615-4150

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✦ Synopsis

Abstract

The allylation of 1,3‐dicarbonyl compounds and malononitrile with aliphatic allylic substrates is achieved under mild conditions in the presence of new ruthenium catalysts. The ruthenium complex [Ru(C~5~Me~5~)(2‐quinolinecarboxylato)(CH~2~CHCH‐n‐Pr)] [BF~4~] as a precatalyst, allows the synthesis of mono‐allylated branched derivatives. On the other hand, the parent complex [Ru(C~5~Me~5~)(MeCN)~3~] [PF~6~] as a precatalyst, straightforwardly favours the bis‐allylation of the procarbonucleophiles leading to bis‐allylated bis‐linear products. The involvement of the two precatalysts provides a sequential synthesis of unsymmetrical mixed linear‐branched bis‐allylated derivatives.

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