• Media type: E-Article
  • Title: Catalytic Enantioselective Synthesis of a 3‐Aryl‐3‐benzyloxindole (=3‐Aryl‐3‐benzyl‐1,3‐dihydro‐2H‐indol‐2‐one) Exhibiting Antitumor Activity
  • Contributor: Katayev, Dmitry; Kündig, E. Peter
  • imprint: Wiley, 2012
  • Published in: Helvetica Chimica Acta
  • Language: English
  • DOI: 10.1002/hlca.201200477
  • ISSN: 0018-019X; 1522-2675
  • Keywords: Inorganic Chemistry ; Organic Chemistry ; Physical and Theoretical Chemistry ; Drug Discovery ; Biochemistry ; Catalysis
  • Origination:
  • Footnote:
  • Description: <jats:title>Abstract</jats:title><jats:p>A palladium‐catalyzed intramolecular <jats:italic>α</jats:italic>‐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 (3<jats:italic>R</jats:italic>)‐6‐chloro‐3‐(3‐chlorobenzyl)‐1,3‐dihydro‐3‐(3‐methoxyphenyl)‐2<jats:italic>H</jats:italic>‐indol‐2‐one ((<jats:italic>R</jats:italic>)‐<jats:bold>5</jats:bold>). This oxindole, in racemic form, had been shown previously to be an anticancer agent. (<jats:italic>R</jats:italic>)‐<jats:bold>5</jats:bold> was obtained with an overall yield of 45% and with 96% enantioselectivity.</jats:p>