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Isoindolinone Synthesis: Selective Dioxane-Mediated Aerobic Oxidation of Isoindolines.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2019 Jan 18; Vol. 84 (2), pp. 1025-1034. Date of Electronic Publication: 2019 Jan 04. - Publication Year :
- 2019
-
Abstract
- N-Alkyl and N-aryl-isoindolinones were prepared by a dioxane-mediated oxidation of isoindoline precursors. The transformation exhibits unique chemoselectivity for isoindonlines. A chiral tertiary (3°)-benzylic position was not racemized during oxidation, and methyl indoprofen was prepared by late stage oxidation. Mechanistic studies suggest a selective H atom transfer, which avoids many known oxidation (by-)products of isoindolinones.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 84
- Issue :
- 2
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 30571120
- Full Text :
- https://doi.org/10.1021/acs.joc.8b01920