Carbene-Catalyzed Tandem Imine Umpolung-Intramolecular Aza-Conjugate Addition-Oxidation to Access N-Substituted Isoindolinones (original) (raw)
Jakkula Ramarao, Purna Chandra Behera, Manyam Subbi Reddy, Surisetti Suresh*
*CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India, Email: surisetti
iict.res.in
J. Ramarao, P. C. Behera, M. S. Reddy, S. Suresh, J. Org. Chem., 2024, 89, 414-424.
DOI: 10.1021/acs.joc.3c02187
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Abstract
A N-heterocyclic carbene (NHC)-catalyzed synthesis of _N_-substituted isoindolinone acetates proceeds through a tandem imine umpolung-intramolecular aza-Michael addition followed by oxidation with molecular oxygen in air as the sole oxidant. This method offers atom efficiency, operational simplicity, large-scale syntheses, and mild reaction conditions.
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proposed mechanism
Key Words
isoindolinones,organocatalysis,oxygen
ID: J42-Y2024