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 Elimin
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- 作者：Masahiro Yoshida ; Mika Fujita ; Tooru Ishii ; and Masataka Ihara
- 刊名：Journal of the American Chemical Society
- 出版年：2003
- 出版时间：April 23, 2003
- 年：2003
- 卷：125
- 期：16
- 页码：4874 - 4881
- 全文大小：208K
- 年卷期：v.125,no.16(April 23, 2003)
- ISSN：1520-5126
文摘
A palladium-catalyzed CO2-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 CO2 elimination-fixation. A variety of propargylicalcohols 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. Highlyenantioselective 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 athree-component decomposition-reconstruction process.