ASYMMETRIC RING-OPENING REACTIONS OF SYMMETRICAL N-ACYLAZIRIDINES WITH THIOLS CATALYZED BY CHIRAL DIALKYLTARTRATE-DIETHYLZINC COMPLEXES

The asymmetric ring opening reaction of 1,2-(N-acylimino)cyclohexanes (N-acylaziridines) with some thiols proceeded in the presence of chira l zinc complexes prepared from diethylzinc and dialkyl L-(+)-tartrate to afford trans 2-(N-acylamino)-1-arylthiocyclohexane in up to 93% ee. The enantioselectivity is highly influenced by the molar ratio of the reactants and the nature of chiral dialkyl tartrate. The chemical str ucture of dialkyl L-(+)-tartrate-zinc complex is discussed on their H- 1 NMR spectra and molecular weight. Copyright (C) 1996 Elsevier Scienc e Ltd