Carbamoyl Anion Addition to Azirines

The addition of carbamoyl anions to azirines affords synthetically useful 2-aziridinyl amide building blocks. The reaction scope was explored with respect to both formamide and azirine, and the addition was found to be highly diastereoselective. A one-pot conversion of a ketoxime to an aziridinyl amide was demonstrated. The method was employed to incorporate an aziridine residue into a dipeptide segment.

Automated summary

The addition of carbamoyl anions to azirines provides synthetically useful 2-aziridinyl amide building blocks with high diastereoselectivity. The method was successfully employed for incorporating an aziridine residue into a dipeptide segment.