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Remarkable Solvent Effect on Pd(0)-Catalyzed Deprotection of Allyl Ethers Using Barbituric Acid Derivatives: Application to Selective and Successive Removal of Allyl, Methallyl, and Prenyl Ethers

Hirokazu Tsukamoto*, Takamichi Suzuki, Yoshinori Kondo

*Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki-aza aoba 6-3, Aoba-ku, Sendai 980-8578, Japan, Email:

H. Tsukamoto, T. Suzuki, Y. Kondo, Synlett, 2007, 3131-3132.

DOI: 10.1055/s-2007-992352


Pd(0)-catalyzed deprotection of allyl ethers using barbituric acid derivatives in protic polar solvent such as MeOH and aqueous 1,4-dioxane proceeds at room temperature without affecting a wide variety of functional groups. Control of the reaction temperature allows selective and successive cleavage of allyl, methallyl, and prenyl ethers.

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Key Words

barbituric acid, Pd(0)-catalyzed deprotection, allyl ethers, protic polar solvent, methallyl ethers, prenyl ethers, cleavage of ethers

ID: J60-Y2007-4050