Phosphine-mediated olefination between aldehydes and allenes: an efficient synthesis of trisubstituted 1,3-dienes with high E-selectivity.
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.
Xu
Silong
S
The State Key Laboratory of Elemento-Organic Chemistry and Department of Chemistry, Nankai University, Tianjin 300071, PR China.
Zhou
Lili
L
Zeng
San
S
Ma
Renqin
R
Wang
Zhihong
Z
He
Zhengjie
Z
D000447:Aldehydes / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*
D000447:Aldehydes; D000466:Alkadienes; D000475:Alkenes; D001688:Biological Products; D010720:Phosphines; C025947:propadiene; C044646:phosphine