Photochemical Access to Substituted β-Lactams and β-Lactones via the Zimmerman-O'Connell-Griffin Rearrangement

August Runemark; Mario Martos; Martin Nigríni; Francoise M Amombo Noa; Lars Öhrström; Henrik Sundén

doi:10.1021/acs.orglett.3c01990

Photochemical Access to Substituted β-Lactams and β-Lactones via the Zimmerman-O'Connell-Griffin Rearrangement

Org Lett. 2023 Jul 28;25(29):5520-5524. doi: 10.1021/acs.orglett.3c01990. Epub 2023 Jul 18.

Authors

August Runemark¹, Mario Martos², Martin Nigríni³, Francoise M Amombo Noa¹, Lars Öhrström¹, Henrik Sundén^{1

4}

Affiliations

¹ Department of Chemistry and Chemical Engineering, Chalmers University of Technology, Kemivägen 10, 412 96 Gothenburg, Sweden.
² Organic Chemistry Department and Institute of Organic Synthesis (ISO), University of Alicante, ctra. San Vicente del Raspeig s/n, 03690 Alicante, Spain.
³ Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 43 Prague, Czech Republic.
⁴ Department of Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, 412 96 Gothenburg, Sweden.

Abstract

A photomediated protocol giving facile access to substituted β-lactam and β-lactones is presented. The method realizes, for the first time, the use of the Zimmerman-O'Connell-Griffin (ZOG) rearrangement in [2 + 2] cycloaddition. Products are obtained in high yield with excellent diastereoselectivity under visible light irradiation and under mild reaction conditions.