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

RSC Adv. 2024 Dec 24;14(54):40287-40298. doi: 10.1039/d4ra07780f. eCollection 2024 Dec 17.

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.