Novel enantiopure δ-thiolactones: synthesis, structural characterization, and reactivity studies†

Abstract

A new series of chiral δ-thiolactone derivatives have been prepared. These compounds exemplify the acetalic N–C–S reversibility of fused thiazolidines toward the thermodynamic product. The stereochemistry of the synthesized compounds was elucidated using X-ray crystallography, NOESY spectroscopy, and DFT calculations. The aminolysis reaction of the δ-thiolactone was studied with various alkyl amines, which can open the thioester to yield amido thiols in a single step. This reaction has the potential to be applied in the synthesis of bioactive compounds, polymer chemistry, and dynamic combinatorial chemistry, among others fields.