New developments in the Peterson olefination reaction

2002/04/19 by L. Frances van Staden, David Gravestock, David J. Ager · 3 citations
Chemistry · #Asymmetric Synthesis and Catalysis #Phosphorus compounds and reactions #Synthetic Organic Chemistry Methods

paper · doi:10.1039/a908402i

openalex publication_date 2002/04/19 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/22

Abstract

Noteworthy developments of the Peterson olefination reaction are reviewed. Evidence for both concerted and stepwise mechanisms for the Peterson olefination reaction is presented. The strong affinity of the oxygen anion for the silyl moiety is emphasised when the Peterson olefination reaction takes preference over both the Julia and Wittig reactions in the presence of S- and P-stabilised silyl carbanions. Cerium-mediated Peterson methylenation reactions are discussed.

Citations

• The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects

Cited by

• The modified Julia olefination: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds
• Stereocontrolled Total Synthesis of Tetrodotoxin from myo- Inositol and D-Glucose by Three Routes: Aspects for Constructing Complex Multi-Functionalized Cyclitols with Branched-Chain Structures
• Peterson olefination [wikipedia]