Stereoselective 1,3-dipolar cycloadditions of thioketones to carbohydrate-derived nitrones
作者： Grzegorz Mlostoń , Aleksandra Michalak , Andrzej Fruziński , Marcin Jasiński
DOI: 10.1016/J.TETASY.2016.08.007
关键词: Stereoselectivity 、 Glyceraldehyde 、 Proton NMR 、 Chemistry 、 Steric effects 、 Enantiopure drug 、 Carbohydrate 、 Dissociation constant 、 Nitrone 、 Stereochemistry
摘要: Abstract 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 spectroscopic data supplemented by X-ray diffraction analysis the major products confirmed anti-configuration derived from d -glyceraldehyde and l -erythrose-functionalized sugar moiety at C atom. In case model benzaldehyde-derived nitrone decorated N atom carbohydrate auxiliary, also for -erythrose-derived cyclic nitrone, reaction sterically crowded 2,2,4,4-tetramethyl-3-thioxocyclobutanone exclusive formation single diastereoisomeric observed indicating an excellent steric match substrates. Dissociation constants (3+2)-cycloadducts were determined 1 H NMR spectroscopy.
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