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Updated: Feb 14, 2026

Curation of Computational Chemical Libraries Demonstrated with Alpha-Amino Acids
Published on: April 13, 2022
Photochemical cyclization of α-amino esters to access 3-azetidinones
Meemie U Hwang1, Achyut Gogoi2,3, Matthew Scurria3
1Department of Chemistry, Northwestern University Evanston IL 60208 USA scheidt@northwestern.edu.
Abstract:
A light-driven cyclization of readily available α-amino esters to 3-azetidinones has been developed. This method leverages chromophore activation with the acyl imidazole to generate the triplet diradical species under mild conditions without the need for photosensitizers or transition metals. A selective hydrogen atom transfer event, followed by intramolecular Norrish-Yang radical coupling occurs to yield the N-heterocycle, with facile elimination of the imidazole group to access the 3-azetidinone. Computational calculations reveal the role of the protecting group in favoring the Norrish-Yang cyclization pathway.
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