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Communication | Special issue | Vol 64, No. 1, 2004, pp.41-44
Published online, 20th August, 2004
DOI: 10.3987/COM-04-S(P)20
Palladium-catalyzed Insertion-Cyclization Reaction of 2,3-Allenols with Aryl Iodides in Water: Synthesis of 1-Arylvinyl-substituted Epoxides

Masahiro Yoshida,* Takayuki Ishii, Takahiro Gotou, and Masataka Ihara*

*Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan


A methodology for the synthesis of substituted epoxides in water has been described. The reactions of 2,3-dienyl alcohols with aryl iodides in the presence of palladium catalyst in water afford the 1-arylvinyl-substituted epoxides. It is clear that water-soluble ligand TPPDS is suitable for the reaction, and various epoxides are produced in moderate to good yields.