The direct preparation of a range of variously substituted chiral tert-butylsulfinylketimines was achieved in good yield (41-90%), with relatively rapid reaction times (4-15 hours); their synthetic application was examined through the reaction with the ylides derived from trimethylsulfonium iodide and S-allyl tetrahydrothiophenium bromide, affording convenient access to a diverse range of highly substituted chiral aziridines in up to 78% yield and > 90% d.e.

[reaction: see text] The preparation of a range of alkyl and aryl chiral vinyl aziridines was achieved in high yield and stereoselectivity, and with excellent diastereoselectivity, by reaction of tert-butylsulfinylimines with the ylide derived from S-allyl tetrahydrothiophenium bromide.

The reaction of dimethylsulfonium methylide with a range of aromatic, heterocyclic and aliphatic tert-butylsulfinyl imines is presented. Aziridines were formed in 63-84% yield and 77-95% diastereomeric excess.