Photo by eriic from unsplash
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… Click to show full 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).
Journal Title: Journal of the American Chemical Society
Year Published: 2022
Link to full text (if available)
Share on Social Media: Sign Up to like & get
recommendations!