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Palladium-catalysed cascade ring expansion reaction of cyclobutanols that have a propargylic moiety with nucleophiles
Authors:Yoshida Masahiro  Komatsuzaki Yuki  Nemoto Hideo  Ihara Masataka
Institution:Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai, 980-8578, Japan.
Abstract: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.
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