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Catalytic Enantioselective Synthesis of a 3-Aryl-3-benzyloxindole (=3-Aryl-3-benzyl-1,3-dihydro-2H-indol-2-one) Exhibiting Antitumor Activity

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Published in Helvetica Chimica Acta. 2012, vol. 95, no. 11, p. 2287-2295
Abstract A palladium-catalyzed intramolecular α-arylation of an amide in the presence of a bulky chiral N-heterocyclic carbene ligand is the key step in the first catalytic synthesis of (3R)-6-chloro-3-(3-chlorobenzyl)-1,3-dihydro-3-(3-methoxyphenyl)-2H-indol-2-one ((R)-5). This oxindole, in racemic form, had been shown previously to be an anticancer agent. (R)-5 was obtained with an overall yield of 45% and with 96% enantioselectivity.
Keywords Indolin-2-one derivativeEnantioselective synthesisAnticancer agents
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Other version: http://doi.wiley.com/10.1002/hlca.201200477
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KATAYEV, Dmitry, KUNDIG, Ernst Peter. Catalytic Enantioselective Synthesis of a 3-Aryl-3-benzyloxindole (=3-Aryl-3-benzyl-1,3-dihydro-2H-indol-2-one) Exhibiting Antitumor Activity. In: Helvetica Chimica Acta, 2012, vol. 95, n° 11, p. 2287-2295. https://archive-ouverte.unige.ch/unige:24335

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Deposited on : 2012-12-05

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