Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Geometry Driven Intramolecular Oxidative Cyclization of Enamides: An Umpolung Annulation of Primary Benzamides with Acrylates for the Synthesis of 3-Methyleneisoindolin-1-ones

Geometry Driven Intramolecular Oxidative Cyclization of Enamides: An Umpolung Annulation of Primary Benzamides with Acrylates for the Synthesis of 3-Methyleneisoindolin-1-ones
Prasad V. Bharatam, Mandeep Kaur Hunjan, Deepika Kathuria, Rohan A. Bhimpuria, Joydev K. Laha
A palladium-catalyzed tandem oxidative annulation of primary benzamides with acrylates via intermolecular N-alkenylation followed by intramolecular C-alkenylation yielded a stereoselective synthesis of (E)-3-methyleneisoindolin-1-ones. The study unveils, for the first time, that only E-enamides could undergo intramolecular oxidative cyclization under the optimized conditions to give isoindolinones. The current strategy represents an umpolung strategy when compared to the literature approaches that use benzamides.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00966

DOI: 10.1021/acs.joc.7b00966

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