Gallium-mediated allyl transfer from bulky homoallylic alcohol to aldehydes via retro-allylation: stereoselective synthesis of both erythro- and threo-homoallylic alcohols.
Retro-allylation of bulky gallium homoallylic alkoxides occurs to generate (Z)- and (E)-crotylgallium reagents stereospecifically, starting from erythro- and threo-homoallylic alcohols, respectively. The (Z)- and (E)-crotylgallium reagents immediately reacted with aromatic aldehydes to afford the corresponding erythro- and threo-homoallylic alcohols, respectively. [reaction: see text]
Hayashi
Sayuri
S
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
Hirano
Koji
K
Yorimitsu
Hideki
H
Oshima
Koichiro
K