Asymmetric ring opening reactions of symmetrical N-acylaziridines with thiols catalyzed by chiral dialkyl tartrate-diethylzinc complexes

Article abstract of DOI:10.1016/0040-4020(96)00370-5

The asymmetric ring opening reaction of 1,2-(N-acylimino)cyclohexanes (N- acylaziridines) with some thiols proceeded in the presence of chiral zinc complexes prepared from diethylzinc and dialkyl L-(+)-tartrate to afford trans 2-(N-acylamino)-1-arylthiocyclohexane in up to 93% cc. The enantioselectivity is highly influenced by the molar ratio of the reactants and the nature of chiral dialkyl tartrate. The chemical structure of dialkyl L-(+)-tartrate-zinc complex is discussed on their ¹H NMR spectra and molecular weight.