- Isoindolinone Synthesis: Selective Dioxane-Mediated Aerobic Oxidation of Isoindolines
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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.
- Thapa, Pawan,Corral, Esai,Sardar, Sinjinee,Pierce, Brad S.,Foss, Frank W.
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p. 1025 - 1034
(2019/01/24)
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- Chemoselective amide reductions by heteroleptic fluoroaryl boron Lewis acids
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The heteroleptic borane catalyst (C6F5)2B(CH2CH2CH2)BPin is found to hydrosilylatively reduce amides under mild conditions. Simple tertiary amides can be reduced using Me2EtSiH, whereas tertiary benzamides required a more reactive secondary silane, Et2SiH2, for efficient reduction. The catalytic system described exhibits exceptional chemoselectivity in the reduction of oligoamides and tolerates functionalities which are prone to reduction under similar conditions.
- Peruzzi, Michael T.,Mei, Qiong Qiong,Lee, Stephen J.,Gagné, Michel R.
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supporting information
p. 5855 - 5858
(2018/06/13)
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- Integrated catalytic C-H transformations for one-pot synthesis of 1-arylisoindoles from isoindolines via palladium-catalyzed dehydrogenation followed by C-H arylation
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A one-pot conversion of isoindolines to 1-arylisoindoles was established from palladium-catalyzed cascade C-H transformations, that is, the dehydrogenation of isoindolines to give isoindoles, with subsequent C-H arylation of the isoindoles.(Figure Presented)
- Ohmura, Toshimichi,Kijima, Akihito,Suginome, Michinori
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supporting information; scheme or table
p. 1238 - 1241
(2011/05/03)
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- New formation of 4,5,6,7-tetrahydroisoindoles
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The high-yield syntheses of 4,5,6,7-tetrahydro-isoindoles from N-substituted isoindolines under palladium catalyzed hydrogenation conditions are reported. Mechanistic study with deuterated and saturated substrates show extensive H/D exchange and the essence of aromaticity in this transformation.
- Hou, Duen-Ren,Hsieh, Yih-Dar,Hsieh, Yi-Wei
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p. 5927 - 5929
(2007/10/03)
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- 1,2-DIHYDROISOINDOLINES FROM INTRAMOLECULAR CYCLOADDITION OF N-ALLYL-2-FURFURYLAMINE HALOHYDRATES
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A number of 1,2 Dihydroisoindolines have been directly obtained from the corresponding allylfurfurylamine hydroclorides.
- Hernandez, J. E.,Fernandez, S.,Arias, G.
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p. 2055 - 2062
(2007/10/02)
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- Base-catalysed Rearrangements involvung Ylide Intermediates. Part 8. The Preparation and Some Reactions of Stable Ammonium Ylides
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The carbonyl-stabilised ammonium ylides (3), (12a-n), and (14a-c) were obtained from the reaction of the corresponding ammonium halides (1), (13a-n), and (15a-c) with sodium hydroxide in water or aqueous methanol.The ylides, which were characterised by their molecular formulae and spectroscopic properies, regenerated quaternary ammonium bromides on treatment with hydrobromic acid.In general the reactions of the ammonium ylides resemble those of the corresponding sulphonium ylides.Thus ylides having a suitable migrating group (ArCH2) undergo a Stevens rearrangement on heating, and other ylides fragment to give a tertiary amine and products containing the PhCOCH grouping.A number of ylides reacted with dimethyl acetylenedicarboxylate to give the furans (32).The ylides (14b and c) with phenyl isocyanate gave the phenylcarbamoyl-substituted ylides.
- Jemison, Robert W.,Mageswaran, Sivapathasuntharam,Ollis, W. David,Sutherland, Ian O.,Thebtaranonth, Yodhathai
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p. 1154 - 1164
(2007/10/02)
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