Preparative and Analytical Enantiomer Separation of Some δ4-1,3-Thiazoline-2-tiones on Swollen Microcrystalline Triacetylcellulose (TAC)

Article abstract of DOI:10.1021/jo00214a022

A number of thiazoline-2-thiones have been resolved by chromatography on swollen microcrystalline triacetylcellulose (TAC) with ethanol as eluent.It was found that the substitution pattern (R₄ and R₅) and the conformation of R₃ of the thiazoline-2-thione ring had a great influence on the enantiomeric resolution.When R₃ has a phenyl group the R configuration is always eluted first.However, the elution order of the esters depends on the substituents (R₄ and R₅) of the thiazoline-2-thione ring.When R₃ had a carboxylic acid residue no resolutions were obtained.Three com pounds (2a, 2b, and 2c) were resolved into their enantiomers in a preparative scale.In spite of relatively small R₈ values, completely pure enantiomers could be obtained by a recycling technique.