Peterson olefination

Definition: A carbon-carbon coupling reaction in which an alpha-silyl carbanion reacts with an aldehyde or a ketone to give an alkene, proceeding via a beta-hydroxysilane. The stereochemistry of the alkene can be controlled by treating the intermediate with acid or base.

ID: RXNO:0000080


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Articles referencing this term

Caesium fluoride-promoted Stille coupling reaction: an efficient synthesis of 9Z-retinoic acid and its analogues using a practical building block
Takashi Okitsu, Kinya Iwatsuka and Akimori Wada, Chem. Commun., 2008 , 6330
DOI: 10.1039/b813760a

Cobalt-catalysed hydrovinylation as the key step in a short synthesis of moenocinol
Gerhard Hilt and Jonas Treutwein, Chem. Commun., 2009 , 1395
DOI: 10.1039/b822023a

A novel and efficient method for the olefination of carbonyl compounds with Grignard reagents in the presence of diethyl phosphite
Tongqiang Wang, Yuanyuan Hu and Songlin Zhang, Org. Biomol. Chem., 2010 , 8 , 2312
DOI: 10.1039/c001931c