4.7 Article

An Unexpected N-Heterocyclic Carbene-Catalyzed Annulation of Enals and Nitroso Compounds

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 4, Pages 1744-1746

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo802515g

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Funding

  1. Ministry of Education in Singapore [ARC12/07, T206B3225]
  2. Nanyang Technological University [RG53/07, RG140/06]

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The N-heterocyclic carbene (NHC)-catalyzed annulation of enals with nitroso compounds in the presence of DBU in THF has been described. Unexpected seven-membered 4-azalactones were formed according to a process involving a 1,2-Bamberger-type rearrangement.

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