Palladium-catalysed cascade ring expansion reaction of cyclobutanols that have a propargylic moiety with nucleophiles.
Cascade ring rearrangement of four-membered ring systems containing various propargylic components by a palladium catalyst is described. The reactions of cyclobutanols that have a propargylic carbonate moiety with phenols as nucleophiles produce phenoxy-induced cyclopentanones in high yields. The reactions proceed in a regio- and diastereoselective manner to afford the substituted cyclopentanones with high selectivities. Imides also act as nucleophiles to produce the imidyl-induced products. Propargylic bromide successfully reacts with sodium alkoxides to produce the corresponding products in good yields.
Yoshida
Masahiro
M
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai, 980-8578, Japan.
Komatsuzaki
Yuki
Y
Nemoto
Hideo
H
Ihara
Masataka
M