4.8 Article

Catalytic Asymmetric Synthesis of 3,3′-Diaryloxindoles as Triarylmethanes with a Chiral All-Carbon Quaternary Center: Phase-Transfer-Catalyzed SNAr Reaction

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 24, Pages 6220-6223

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201403046

Keywords

arylation; asymmetric catalysis; organocatalysis; phase-transfer catalysis; synthetic methods

Funding

  1. JSPS
  2. MEXT (Japan)
  3. Grants-in-Aid for Scientific Research [26220803, 21000006, 25870335] Funding Source: KAKEN

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Catalytic asymmetric synthesis of unsymmetrical triarylmethanes with a chiral all-carbon quaternary center was achieved by using a chiral bifunctional quaternary phosphonium bromide catalyst in the SNAr reaction of 3-aryloxindoles under phase-transfer conditions. The presence of a urea moiety in the chiral phase-transfer catalyst was important for obtaining high enantioselectivity in this reaction.

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