Issue 54, 2024

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.

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

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Article information

Article type
Paper
Submitted
31 অক্টো 2024
Accepted
13 ডিচে 2024
First published
24 ডিচে 2024
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2024,14, 40287-40298

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

M. Rodríguez Saravia, V. Martínez, F. Vairoletti, M. Macías, D. Davyt, G. Hernández Dossi and G. Mahler, RSC Adv., 2024, 14, 40287 DOI: 10.1039/D4RA07780F

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