Journal of Organic Chemistry p. 2519 - 2521 (1985)
Update date:2022-08-11
Topics:
Isaksson, Roland
Roschester, Jan
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.
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