1,2-Asymmetric induction in a new tandem of (33)-sigmatropic rearrangement of chiral thiocyanates and intramolecular amine addition to N=C=S group

Article abstract of DOI:10.1016/S0040-4039(96)02429-X

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 AMI calculations demonstrate that the observed diastereoselectivity is entirely consistent with the energy difference between diastereomeric transition states of heterocyclisation step.