Asymmetric aziridination by reaction of chiral N-sulfinylimines with sulfur ylides: Stereoselectivity improvement by use of tert-butylsulfinyl group as chiral auxiliary

Article abstract of DOI:10.1016/S0957-4166(96)00448-X

Chiral tert-butylsulfinyl group has been shown to be the chiral auxiliary of choice for the asymmetric aziridination of N-sulfinyliminas. Moreover, the sense of the asymmetric induction can be tuned in two ways: the chirality at the tert-butylsulfinyl Sulfur, or the nature of the methylene transfer reagent used. Thus, both aziridines 10(S(S),S) and 10(R(S),R), epimeric at C-2, were obtained in enantiomerically pure form by a single crystallisation (75% yield).