4.8 Article

Conjugate Addition-Initiated Nazarov Cyclization

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 32, Pages 12454-12457

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja205440x

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Funding

  1. National Institutes of Health [NIGMS R01 GM079364]
  2. ARRA supplement [3R01GM079364-03S2]

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A reaction sequence involving the 1,6-conjugate addition of a nucleophile to a dienyl diketone followed by Nazarov cyclization is described. Several nucleophiles are identified as competent initiators for the sequence. A different reaction outcome is observed when catalytic amounts of nucleophile are employed, involving elimination of the nucleophile after the electrocyclization.

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