The Norrish-Yang cyclization of beta-ketoformamides to provide 3-phenyl-3-hydroxy-beta-lactams is reported. Investigations center on: i. the stream-lined, scalable, three-step synthesis of beta-ketoformamides from commercially available 2-halo-acetophenones, ii. the identification and optimization of photocyclization reaction conditions (solvent, reaction time, light source), and iii. the effect of electron-donating and electron-withdrawing <i>o</i>- and <i>p</i>-phenyl substitution on the success of 3-hydroxy-beta-lactam formation. Taken collectively, the presented study represents one of the only protecting group-free methods for the formation of 3-hydroxy-beta-lactams and can serve as a necessary resource for the incorporation of photocyclization strategies to generate 3-hydroxy-beta-lactam systems en route to the synthesis of more complex biologically active small molecules.

Norrish-Yang cyclizations of beta-ketoformamides: A photochemical approach to 3-hydroxy-beta-lactams

256th National Meeting (2018)

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