Stereodefined construction of trisubstituted alkenes by direct coupling reaction of allylating agents, alkynes, and organoboranes.
Tandem reaction: The Pd-catalyzed three-component coupling reaction of an allylic alcohol, terminal alkyne, and organoborane to give (E)-1-substituted 2-alkyl-1,4-pentadienes, involving geminal allylation and alkylation at the acetylenic terminal carbon, is described. Bis-diene undergoes a similar multicomponent coupling reaction with acetylene and organoborane, involving cyclization of bis-π-allylpalladium, to form trans-allyl pentadienyl cyclic and heterocyclic compounds with excellent regio- and stereoselectivities (see scheme).
Graduate School of Engineering, Nagasaki University, 1-14 Bunkyo machi, Nagasaki 852-8521, Japan.
Masahiro
M
Fukushima
Daiki
D
Takushima
Hideaki
H
Satomura
Gen
G
Onodera
Masanari
M
Kimura