Phosphine-Mediated Olefination between Aldehydes and Allenes: An Efficient Synthesis of Trisubstituted 1,3-Dienes with High E-Selectivity
Organic Letters2009Vol. 11(15), pp. 3498–3501
Citations Over TimeTop 10% of 2009 papers
Abstract
The phosphine-mediated olefination of aldehydes with electron-deficient allenes to afford trisubstituted conjugated dienes in fair to excellent yields with high E-selectivity is described. The reaction represents a new reactivity pattern of allenes with aldehydes and also provides a highly stereoselective synthetic method for preparing conjugated dienes. In the reaction, the phosphine acts as a nucleophilic promoter to generate in situ an active phosphorus ylide which mediates the intermolecular olefination.
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