Palladium-catalyzed allylation of aryl halides with homoallyl alcohols bearing a trisubstituted double bond: application to chirality transfer from hydroxylated carbon to benzylic one.
A facile route to homoallyl alcohols bearing a trisubstituted double bond has been devised. The palladium-catalyzed reactions of aryl halides with the alcohols thus synthesized result in regiospecific allyl transfer from the alcohols to aryl halides via retro-allylation, providing allylarenes having two substituents at the 1 and 2 positions of the allyl moiety. Optically active homoallyl alcohols transfer their chirality at the hydroxylated carbon to the benzylic carbon of the product.
Wakabayashi
Ryota
R
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
Fujino
Daishi
D
Hayashi
Sayuri
S
Yorimitsu
Hideki
H
Oshima
Koichiro
K