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

被引：27

作者：

Tsukamoto, Hirokazu ^{[1
]}

Suzuki, Takamichi ^{[1
]}

Kondo, Yoshinori ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan

来源：

SYNLETT | 2007年 / 20期

关键词：

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

D O I：

10.1055/s-2007-992352

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. A study of ligand effects on the deprotection reveals that the improved reactivity in MeOH results from the accelerated oxidative addition to Pd(0).

引用

页码：3131 / 3136

页数：6

共 4 条

[1] Chromatography-free Pd-catalyzed deprotection of allyl ethers using PS-DEAM as a scavenger of boronic acids and Pd catalyst
Tsukamoto, Hirokazu
Suzuki, Takamichi
Sato, Masanori
Kondo, Yoshinori
TETRAHEDRON LETTERS, 2007, 48 (48) : 8438 - 8441
[2] Facile and selective cleavage of allyl ethers based on palladium(0)-catalyzed allylic alkylation of N,N′-dimethylbarbituric acid
Tsukamoto, H
Kondo, Y
SYNLETT, 2003, (07) : 1061 - 1063
[3] SELECTIVE CLEAVAGE OF THE ALLYL AND ALLYLOXCARBONYL GROUPS THROUGH PALLADIUM-CATALYZED HYDROSTANNOLYSIS WITH TRIBUTYLTIN HYDRIDE - APPLICATION TO THE SELECTIVE PROTECTION-DEPROTECTION OF AMINO-ACID DERIVATIVES AND IN PEPTIDE-SYNTHESIS
DANGLES, O
GUIBE, F
BALAVOINE, G
LAVIELLE, S
MARQUET, A
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22): : 4984 - 4993
[4] Dehydrative Allylation of Alcohols and Deallylation of Allyl Ethers Catalyzed by [CpRu(CH3CN)3]PF6 and 2-Pyridinecarboxylic Acid Derivatives. Effect of π-Accepting Ability and COOH Acidity of Ligand on Reactivity
Tanaka, Shinji
Saburi, Hajime
Hirakawa, Takuya
Seki, Tomoaki
Kitamura, Masato
CHEMISTRY LETTERS, 2009, 38 (02) : 188 - 189

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