Conformational analysis and selective hydrolysis of 2,5-disubstituted-1,3-dioxane-2-carboxylic acid esters

Tetsuji Harabe, Takatoshi Matsumoto, Takayuki Shioiri

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

5-Alkyl-2-methyl-2-carbomethoxy-1,3-dioxanes were found to have a cis preferential configuration in the equilibrium state, and the ester hydrolysis rate of the trans-isomers was faster than that of the cis-isomers. Conformational analysis and charge calculation of the carbomethoxy group in both dioxanes elucidated this selectivity.

Original languageEnglish
Pages (from-to)1443-1446
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number8
DOIs
Publication statusPublished - 2007 Feb 19

Keywords

  • 1,3-Dioxane derivative
  • Charge calculation
  • Conformational analysis
  • Selective hydrolysis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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