Synthesis and dynamic stereochemistry of 4-aryl-thiomorpholine-3,5-dione derivatives

Abstract A series of new N-aryl-substituted thiomorpholine-3,5-diones were synthesized. Crystal structures of seven compounds were established on the basis of X-ray crystallography. Stable at room temperature diastereomers were detected for (2-phenyl)-substituted derivatives using 1 H NMR. The dynamic stereochemistry of compound 36 was studied with variable-temperature 1 H NMR and the mechanism of diastereomers interconversion was proposed on the basis of quantum chemical calculations.