Access to β-Lactams via Iron-Catalyzed Olefin Oxyamidation Enabled by the π-Accepting Phthalocyanine Ligand.

Abstract

Herein, we report the development of an iron-catalyzed olefin oxyamidation by utilizing tethered dioxazolones as the nitrenoid precursor to produce valuable β-lactam scaffolds. Mechanistic studies revealed that a relatively strong π-accepting ability of the phthalocyanine ligand is critical in generating the key triplet iron-imidyl radical intermediate to enable the 4-exo-trig-lactamization with the incorporation of oxygen nucleophiles in high diastereoselectivity. This cyclization approach was readily extended to the highly efficient γ-lactam synthesis (TON > 300).