4.8 Article

Stereoselective Oxindole Synthesis by Palladium-Catalyzed Cyclization Reaction of 2-(Alkynyl)aryl Isocyanates with Amides

Journal

ORGANIC LETTERS
Volume 11, Issue 10, Pages 2141-2143

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol900759f

Keywords

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Funding

  1. MEXT [20037032]
  2. Young Scientists [20750078]
  3. Mizuho Foundation for the Promotion of Sciences
  4. Uehara Memorial Foundation
  5. Global COE Program Integrated Materials Science [B-09]
  6. Grants-in-Aid for Scientific Research [20037032, 20750078] Funding Source: KAKEN

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A new cyclization reaction occurred on treatment of 2-(alkynyl)aryl isocyanates with amides in the presence of a palladium(0)/diphosphine catalyst to stereoselectively form 3-(amidoalkylidene)oxindoles. A carbon-nitrogen bond as well as a carbon-carbon bond were simultaneously introduced onto the alkyne moiety to construct an oxindole skeleton with stereoselective placement of the amino substituent cis to the carbonyl group.

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