4.8 Article

Carbene-Catalyzed [4+2] Annulation of 2H-Azirine-2carboxaldehydes with Ketones via Azolium Aza-Dienolate Intermediate

Journal

ORGANIC LETTERS
Volume 20, Issue 23, Pages 7641-7644

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03378

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Funding

  1. National Natural Science Foundation of China [21871160, 21672121]
  2. Thousand Plan Youth Program of China
  3. Tsinghua University
  4. Bayer Investigator Fellow
  5. Fellowship of Tsinghua-Peking Centre for Life Sciences (CLS)

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A new carbene-catalyzed [4 + 2] annulation of 2H-azirine-2-carbaldehydes with ketones was developed, thus providing the 2,3-dihydro-6H-1,3-oxazin-6-one core structures with broad scope and good to excellent yields. Notably, the azolium aza-dienolates generated from the addition of NHCs to 2H-azirines are first uncovered.

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