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Research Article
Catalytic Enantioselective Synthesis of a 3-Aryl-3-benzyloxindole (=3-Aryl-3-benzyl-1,3-dihydro-2H-indol-2-one) Exhibiting Antitumor Activity
Article first published online: 19 NOV 2012
DOI: 10.1002/hlca.201200477
Copyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland
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Additional Information
How to Cite
Katayev, D. and Kündig, E. P. (2012), Catalytic Enantioselective Synthesis of a 3-Aryl-3-benzyloxindole (=3-Aryl-3-benzyl-1,3-dihydro-2H-indol-2-one) Exhibiting Antitumor Activity. HCA, 95: 2287–2295. doi: 10.1002/hlca.201200477
Publication History
- Issue published online: 19 NOV 2012
- Article first published online: 19 NOV 2012
- Manuscript Received: 15 AUG 2012
- Abstract
- References
- Cited By
Keywords:
- Indolin-2-one derivative;
- Enantioselective synthesis;
- Anticancer agents
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.