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Diazo Strategy for Intramolecular Azirine Ring Expansion: Rh(II)-Catalyzed Synthesis of 2-Hydroxy-3-oxo-2,3-dihydro-1H-pyrrole-2-carboxylates

Timur O. Zanakhov, Ekaterina E. Galenko, Mikhail S. Novikov and Alexander F. Khlebnikov*

*Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Naberezhnaya, St. Petersburg 199034, Russia, Email: a.khlebnikovspbu.ru

T. O. Zanakhov, E. E. Galenko, M. S. Novikov, A. F. Khlebnikov, J. Org. Chem., 2022, 87, 15598-15607.

DOI: 10.1021/acs.joc.2c02177



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Abstract

Azirinyl-substituted diazodicarbonyl compounds, prepared from diazoacetylazirines, were converted in excellent yields to 2-hydroxy-3-oxo-2,3-dihydro-1H-pyrrole-2-carboxylates under Rh catalysis in the presence of water.

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Key Words

N-heterocycles


ID: J42-Y2022