title: A novel methodology for the synthesis of cyclic carbonates based on the palladium-catalyzed cascade reaction of 4-methoxycarbonyloxy-2-butyn-1-ols with phenols, involving a novel carbon dioxide elimination-fixation process.
abstract: A palladium-catalyzed CO(2)-recycling reaction has been developed. Reaction of 4-methoxycarbonyloxy-2-butyn-1-ols with phenols, carried out in the presence of a palladium catalyst, produces phenoxy-substituted cyclic carbonates by way of a pathway involving a CO(2) elimination-fixation. A variety of propargylic alcohols and phenols participate in these reactions which yield cyclic carbonates with high efficiencies. Stereoselective construction of trans-cyclic carbonates is achieved by using nonsymmetric substrates. Highly enantioselective reactions occur when (S)-BINAP is used as a ligand. Reaction of 4-phenoxycarbonyloxy-2-butyn-1-ol in the presence of the palladium catalyst yields the corresponding cyclic carbonates via a three-component decomposition-reconstruction process.
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Yoshida
authors.forename: Mika
authors.initials: M
authors.lastname: Fujita
authors.forename: Tooru
authors.initials: T
authors.lastname: Ishii
authors.forename: Masataka
authors.initials: M
authors.lastname: Ihara