Science of Synthesis

Aggarwal, V. K.; McGarrigle, E. M.; Shaw, M. A., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 332.

In Corey and Chaykovskyʼs second publication on the ylide-mediated epoxidation of aldehydes they demonstrated that the reaction could also be applied to imines to afford aziridines, employing either trimethylsulfoxonium methylide or trimethylsulfonium methylide, the latter providing the higher yield of 91% of aziridine ‌43‌ in the reaction of N-phenylbenzaldimine (‌Scheme 25‌).[‌75‌]

‌Meeeee 88‌ Mee-Meeee–Meeeeeeeee Meeeeeeeeeeeee[‌88‌]

Mee eeeeee eee eeeeeeeeeeeee eeeeee ee eeeeeeee ee eeee ee e eeeeeeeee eeee,[‌88‌–‌88‌] eeeee eee ee eeeeee ee eeee,[‌88‌] eee ee eeee eee eeeeeeeeeeee eeeeeeeee ee Meeeeee ‌8.8.8.8.8‌, eeee eee eeee ee eeeeeeeee eeeeeee eee eeeeeeee ee e eeeeeeeeeeeeee eeee e eeeeeee.[‌88‌,‌88‌] Meeee eeeeeeeee eeee eee eeee eeeee ee ee eeeeeeeeee ee eee eeeeeeee ee eeeeee eeeee eeee eeeeee eeee eee eeeeeeeee e eeeeeeee eeeeee eeeeeeee ee eee eeeeee.

Mee eeee “eeeeeeeeeeeeee eeeee” ee eeeee eeee ee eeeee ee eeeeee ee eeeee eee eeeeeeee eeeeee ee eeeeeeeeee ee ee eeeeeee ee ee eeeeeeee eeeeee eeeeeeee ee eee eeeeeeeeeeee eeeeee. Meeee eeeeeeeeeeeeee eeeeee eeee ee eeee eeeeeeee ee eeee eeeee eeeeeeeeeeeeeeeeeeee ee eeeeeeee ee eeeeee eeeeeee eeeeeeeeee eeeeee, eeeeeeee eeeeeeeeee eeee eeee eeeeeeee.[‌88‌] Meeee-eeeeeeeeee eeeeee eeeeee eeeeeeeee, eeeeeeee ee eeeee eeeee eee eeeeeeeeeeeeeeeeeeeeee eee eeeeee eeeeeeeee eeee eee eeeeeeee eeeeeeeeeeee.[‌88‌,‌88‌]

Meeeeeee-eeeeeeeeeee eeeeee ee eee eeeeeeee, ee Meeee eeee eeeeeeeee eee eeeeeeee ee eeeeeeee eee eeeee eeeeeeeeeeee eee eeeeeeee eeee eeeeeeeeeeeeee eeeeee. ‌Meeeee 88‌ eeeeeeeeeee eee eeeeeeee ee eeee eeeeeeeeeeeeee eeeeee, eeeeee ee eeeeeeeee ee eeeeeeeee eeeeeeeee eeeee eeee eeee, ee eeeeeeeeeee eeeeee ee eeee eeeeeeeeee ‌88‌.

‌Meeeee 88‌ Meeee Meeeeeeeeeeee eeee Meeeeeeeeeeeee Meeeee Meeeee Meeeeeeee eeee Meeeeeeee Meeee[‌88‌–‌88‌,‌88‌]

‌Meeeeeeeeee 88‌

e Mee eeeeeeeee eeee eee eeeeee ee eeee eeee (M)-MeMM8MM=MMMe eee Me8M.

Meeeee eeeeeee eeee-eeeeeeeeeee eeeeee eeee ee eeeeee eeeeeee eeeeee eeeeeeeeeeeee eee-eeeeeeeeee. Meeee eeee ee eeee eeee eeee eeeeeeee eee e eeeeeee eeeee, ee eee eeee eeeeee eeeeeee eeee eee eeeeeeeeeeeee eeeeeeeee eeeee eeeeee.[‌88‌] Mee eeeeeee eeeeee eee eeee ee eeeeeeee ee eeee eeeeee eeee eeeeeeeeeeeeee eeeeee, eeeee eeeee eeeee eeee eeeeeeee eeeee eeeeeeeeeee, ee eeeee ee ‌Meeeee 88‌. Mee eeee eeeeeeeeeeee ee eeee eeeeee ee eee eee ee eeeee eeeeeeeee. Mee eeeeeeeeeeeeee eeeeee eeeee eee ee eeeeeeeee ee eeee eeee eeeeeeeeeeeeee eeeee ee e eeeee eeeeeeeee (eee Meeeeee ‌8.8.8.8.8‌).[‌88‌] Meeeeeee eeee eeeee eeeeeeeee eee eeee eeee eeeeeeeee eeeee eeeeee eeeeeeeeee eeeeeeee, ee eeee eeee eee eeeeeee eeeeeeee eee. Mee eeeeeee eeeee eee eeeeeeeeee ee eee eeeeeeeeeeeeeeeeeeeeee eeee eee ee eeeeeeee.

‌Meeeee 88‌ Meeee Meeeeeeeeeeee eeee Meeeee Meeeee Meeeeeeee eeee Meeeeeeeeeeeeee[‌88‌,‌88‌]

‌Meeeeeeeeee 88‌

Meeeeeeeeeee Meeeeeeee

8,8-Meeeeeeeeeeee Meeeeeeeee, e.e. ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

MeM (8 eeeee) ee e eeeeeeeeee ee eeeeeee eee eee eeeeee eeee eeeeeee, eee eeeee MMMM (888 eM · eeee−8) eee eeeee. Mee eeeeeeeee eeeeeee eee eeeeeee ee eeeeee eeeee eee eeeeeeeee ee M8 eeeeee (~88 eee). Mee eeee eee eeeeee ee ee, eeeeeee eeee ee eeeee eeeeee ee eeeee MMM, eee eeee eeeeee ee ee eee/eeee eeee. Meee eeeeeeee, e eeee ee eeeeeeeeeeeeeeeeee eeeeee (8 eeeee) ee MMMM (888 eM · eeee−8) eee eeeee, eeeeeee eee eeeeeeeeeee eeeee 8 °M. Mee eee eeeee eee eeeeeeee ee eee eeee eee eeeeeeee, eee eeeee eee eeeee ee e eeee ee MMMM. Meeeeeee eee eeeeeeeee eee eeeeeee eeeeeee ee eee eee/eeee eeee eee eeee eee 88–88 eee ee ee. Mee eeeeeee eee eeeeeee eeee eeeee eeeeeee ee M8M eee eee eeeeeee eee eeeeeeeee eeee eeeeeee, eeeeee eeee M8M, eee eeeee.

Meeeeeeeee ‌88‌; Meeeeee Meeeeeeee eee Meeeeeeeeeeeee Meeeee Meeeeeeee eeee Meeeeeeee Meeee:[‌88‌]

M 88-eM eeeee eeeeeeeeee e eeeeeeee eeeeeee eee eee eeeeeee eeee eeeee (8.8 eeeee), eeeeeeeee eeee (8.8 eeeee), eee MeMM (8 eM). Meeeeeee MMM (8.8 eeeee) eee eeeeeeeeeeee eeeee eeee eeeeeeee. Meeee eee eeeeeeee eee eeeeeeee eeeeeeeee ee MMM, eee eeeeeee eee eeeeeeee eeeeeee e eeeee eeeeee (eeeeeee eeeeeee) ee eeeeee eeeeeeeee eeeee. Mee eeeeeeee eee eeeeeeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee [eeeeeee eeeeeee, eeeeeeeee eeeee (ee 88–88 °M)/MeMMe/Me8M 8:8:8].

Meeeeeeeee ‌88‌; Meeeeee Meeeeeeee eee Meeeeeeeeeeeee Meeeee Meeeeeeee eeee Meeeeeee eee Meeeeee Meeeeeee:[‌88‌]

M 88-eM eeeee eeeeeeeeee e eeeeeeee eeeeeee eee eee eeeeeee eeee eeeee (8.8 eeeee), Me8M (8.8 eeeee), eeeee ee eeeeee eeeeeee (8.8 eeeee), eee MeMM (8 eM). Meeeeeee M8MM8 (8.8 eeeee) eee eeeeeeeeeeee eeeee eeee eeeeeeee. Meeee eee eeeeeeee eee eeeeeeee eeeeeeeee ee MMM, eee eeeeeee eee eeeeeeee eeeeeee e eeeee eeeeee (eeeeeee eeeeeee) ee eeeeee eeeeeeeee eeeee. Mee eeeeeeee eee eeeeeeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee [eeeeeee eeeeeee, eeeeeeeee eeeee (ee 88–88 °M)/MeMMe/Me8M 8:8:8].

References