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

Tetsuji Harabe, Takatoshi Matsumoto, Takayuki Shioiri

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

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 homoanomeric effects will explain the axial preference of the carbomethoxy group and selective hydrolysis to the trans isomers. Furthermore, the calculated stability between the cis and trans isomers is in good agreement with the experimental results in the equilibrium state.

Original languageEnglish
Pages (from-to)4044-4052
Number of pages9
JournalTetrahedron
Volume65
Issue number20
DOIs
Publication statusPublished - 2009 May 16

Keywords

  • 1,3-Dioxane-2-carboxylic acid esters
  • Anomeric effect
  • Conformational analysis
  • Homoanomeric effect
  • Selective hydrolysis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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