Isomerization of Aziridines to Allyl Amines via Titanium and Chromium Cooperative Catalysis

J Org Chem. 2022 Apr 1;87(7):4991-4997. doi: 10.1021/acs.joc.1c03054. Epub 2022 Mar 18.

Abstract

A Ti/Cr cooperative catalyst isomerizes aziridines to allyl amines under mild conditions. The reaction tolerates a broad range of aziridines with various nitrogen substituents. The titanium catalyst is most successful in opening 1,2-disubstituted aziridines, forming radical intermediates in a highly regioselective manner. The chromium catalyst appears to abstract an H from these radical intermediates and then return the H to the titanium system in the form of an H+ and an electron. The reaction is complementary to previous reports on the isomerization of aziridines to allyl amines.