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Diastereoselective C–H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ–lactams

Abstract

We report the development of a diastereoselective palladium-catalyzed C–H carbonylation of unprotected secondary alkylamines to form trans-4,5-disubstituted 2-pyrrolidinones. A carefully balanced mixture of sterically hindered carboxylate and ligands is required for a diasteroselective C–H activation step and a synthetically practical carbonylation process. Interestingly, the ligand cocktail is also capable of influencing the mechanism of the reaction by subtly controlling the position of carbonylation at either the β- or γ-C–H bond with respect to the directing amine motif

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Publication details

The article was received on 28 Jun 2018, accepted on 20 Jul 2018 and first published on 31 Jul 2018


Article type: Edge Article
DOI: 10.1039/C8SC02855A
Citation: Chem. Sci., 2018, Accepted Manuscript
  • Open access: Creative Commons BY license
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    Diastereoselective C–H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ–lactams

    M. J. Gaunt, P. Z. Mao, J. Cabrera-Pardo and J. Peiró Cadahía, Chem. Sci., 2018, Accepted Manuscript , DOI: 10.1039/C8SC02855A

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