Beilstein J. Org. Chem.2012,8, 1443–1451, doi:10.3762/bjoc.8.164
backbone the sulfonimidoyl moiety leads to organocatalysts showing good reactivity in the catalytic desymmetrization of a cyclic meso-anhydride and moderate enantioselectivity in the catalyticasymmetricBiginellireaction. Straightforward synthetic routes provide the newly designed thiourea-sulfoximine
catalysts in high overall yields without affecting the stereohomogeneity of the sulfur-containing core fragment.
Keywords: anhydride opening; catalyticasymmetricBiginellireaction; organocatalysis; sulfoximines; thioureas; Introduction
Since their discovery in the middle of the last century
, enantioenriched dihydropyrimidines could only be obtained by special resolution methods which were not generally applicable. The search for a truly catalyticasymmetricBiginellireaction with high enantiocontrol has proven very challenging for a long time and useful protocols have just recently been developed
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Graphical Abstract
Figure 1:
General structure of sulfoximines 1 and one of the enantiomers of S-methyl-S-phenylsulfoximine ((S)-...