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

Authors

  • Dmitry Katayev,

    1. Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, CH-1211 Geneva, 4, (fax: +41-22-379-3215)
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  • E. Peter Kündig

    Corresponding author
    1. Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, CH-1211 Geneva, 4, (fax: +41-22-379-3215)
    • Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, CH-1211 Geneva, 4, (fax: +41-22-379-3215)

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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.

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