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A series of cycloaliphatic thioketones was reacted with selected enantiopure nitrones bearing carbohydrate-derived moieties leading to 1,4,2-oxathiazolidine derivatives in a highly stereoselective manner. Analysis of spectroscopic data supplemented by X-ray diffraction analysis of the major products confirmed the anti-configuration in the series derived from d -glyceraldehyde and l -erythrose-functionalized nitrones bearing a sugar moiety at the C atom. In the case of the model benzaldehyde-derived nitrone decorated at the N atom with carbohydrate auxiliary, and also for a l -erythrose-derived cyclic nitrone, in the reaction with sterically crowded 2,2,4,4-tetramethyl-3-thioxocyclobutanone the exclusive formation of single diastereoisomeric products was observed indicating an excellent steric match of the substrates. Dissociation constants of selected (3+2)-cycloadducts were determined by 1 H NMR spectroscopy. [ABSTRACT FROM AUTHOR]