Isoindolinone Synthesis: Selective Dioxane-Mediated Aerobic Oxidation of Isoindolines

Autor:	Sinjinee Sardar, Esai Corral, Frank W. Foss, P. Thapa, Brad S. Pierce
Rok vydání:	2018
Předmět:	inorganic chemicals 010405 organic chemistry Organic Chemistry Late stage Indoprofen Isoindoline 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound chemistry medicine Chemoselectivity medicine.drug
Zdroj:	The Journal of Organic Chemistry. 84:1025-1034
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.8b01920
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b104aea1bb503efae3baa6ba59ae20e2 https://doi.org/10.1021/acs.joc.8b01920 Zobrazit plný text záznamu