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  • Title: Phosphine-mediated olefination between aldehydes and allenes: an efficient synthesis of trisubstituted 1,3-dienes with high E-selectivity.
    Author: Xu S, Zhou L, Zeng S, Ma R, Wang Z, He Z.
    Journal: Org Lett; 2009 Aug 06; 11(15):3498-501. PubMed ID: 19580297.
    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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