Journal
HELVETICA CHIMICA ACTA
Volume 95, Issue 11, Pages 2287-2295Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.201200477
Keywords
Indolin-2-one derivative; Enantioselective synthesis; Anticancer agents
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A palladium-catalyzed intramolecular a-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.
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