Abstract
A new synthetic route to diastetereomerically pure 1,3-imidazolidin-2-thiones via a tandem of (3,3)-sigmatropic rearrangement of chiral thiocyanates followed by stereoselective intramolecular amine addition to arising isothiocyanates is reported. The semiempirical AM1 calculations demonstrate that the observed diastereoselectivity is entirely consistent with the energy difference between diastereomeric transition states of heterocyclisation step.
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