Organocatalytic, Organic Oxidant Promoted, Enamine C-H Oxidation/Cyclopropanation Reaction

Herein, we demonstrate that organic, single-electron oxidant in the presence of diarylprolinol silylether type catalyst serves as a tool for the transformation of electron-rich enamines to iminium ions. These iminium ions take part in a subsequent Michael-initiated ring-closure (MIRC) reaction with in situ present nucleophile giving rise to overall cyclopropanation reaction of saturated aldehydes. Stereodefined cyclopropanes are obtained in high yields and selectivities. This one-pot transformation represents the additional example of saturated aldehydes being used in the coupled one-pot processes.

Automated summary

Organic single-electron oxidant in the presence of diarylprolinol silylether type catalyst can transform electron-rich enamines to iminium ions, which then participate in a subsequent Michael-initiated ring-closure reaction with in situ nucleophile to yield stereodefined cyclopropanes from saturated aldehydes. This one-pot transformation exemplifies the use of saturated aldehydes in coupled processes, providing high yields and selectivities.