Tetrahedron

Esters of 2, 5-multisubstituted-1, 3-dioxane-2-carboxylic acid: their conformational analysis and selective hydrolysis

T Harabe, T Matsumoto, T Shioiri

文献索引：Harabe, Tetsuji; Matsumoto, Takatoshi; Shioiri, Takayuki Tetrahedron, 2009 , vol. 65, # 20 p. 4044 - 4052

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被引用次数: 7

摘要

The carbomethoxy group at the C2 position of the 2, 5-multisubstituted 1, 3-dioxanes prefers the axial conformation rather than the equatorial one due to an anomeric effect. The trans isomers of the 5-monosubstituted compounds are more selectively hydrolyzed than the cis isomers. Based on the calculated results, hydrolysis to the trans isomers is attributed to the larger carbonyl charges of the trans than those of the cis isomers. The anomeric and ...