Stereoselective synthesis of 1,2,3,4-tetrasubstituted dienes from allenoates and aldehydes: an observation of phosphine-induced chemoselectivity.
Phosphine-mediated olefination between alpha-substituted allenoates and aldehydes to form 1,2,3,4-tetrasubstituted 1,3-dienes is presented. High levels of chemo- and diastereoselectivity and yield are obtained for a wide scope of substrates with the choice of appropriate phosphines. This reaction evidences the capacity of phosphines in the control of reaction pathways and provides a highly efficient synthetic method for tetrasubstituted conjugated dienes.
Xu
Silong
S
The State Key Laboratory of Elemento-Organic Chemistry and Department of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300071, P.R. China.
Zou
Wen
W
Wu
Guiping
G
Song
Haibin
H
He
Zhengjie
Z
D000447:Aldehydes / Q000737:chemistry; D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000466:Alkadienes; D010720:Phosphines; C044646:phosphine