Stream-lined synthesis of 3-hydroxy-β-lactams: Norrish-Yang type II photocyclizations of β-ketoformamides

Jana L. Markley, Tyler L. Morse, Nigam P. Rath, Timothy A. Wencewicz

Research output: Contribution to journalArticlepeer-review

8 Scopus citations


A photochemical approach to 3-phenyl-3-hydroxy-β-lactams (3-HβLs) is reported. Irradiation of aryl-β-ketoformamides with a UV light band centered at 300 nm provides the corresponding 3-aryl-3-HβLs with good conversion. The scope of the photocyclization is explored with an electronically diverse panel of substrates that provides mechanistic insight supporting a Norrish-Yang type II cyclization. A flexible synthetic route to phenyl-β-ketoformamides, followed by photoirradiation, allows for efficient incorporation of the β-lactam pharmacophore into aromatic organic scaffolds. Taken collectively, the improved and optimized synthetic route to provide both β-ketoformamides and 3-HβLs—in combination with the expanded analysis of substrate scope and limitations—reported herein will serve as a necessary reference for the direct, atom-economical, radical-mediated installation of 3-HβL scaffolds en route to the generation of other biologically active small molecules.

Original languageEnglish
Pages (from-to)2743-2753
Number of pages11
Issue number22
StatePublished - May 31 2018


  • 3-Hydroxy-β-lactams
  • Norrish-Yang cyclization
  • Photocyclization
  • Radical chemistry
  • β-Ketoformamide formation
  • β-Lactam synthesis


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