4.7 Article

Palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes: facile synthesis of bicyclo[4.1.0]heptan-5-ones

Journal

CHEMICAL COMMUNICATIONS
Volume 51, Issue 64, Pages 12819-12822

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5cc04300j

Keywords

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Funding

  1. Natural Science Foundation of China [21172060, 21472039, 21402046]
  2. Specialized Research Fund for the Doctoral Program of Higher Education [20120161110041]
  3. Hunan Provincial Natural Science Foundation of China [13JJ2018]

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We here describe a new palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes at room temperature using tBuONO as an oxidant for the synthesis of 3-bicyclo[4.1.0]heptan-5-ones. This cascade strategy involves the hydration, cyclization and cyclopropanation sequence, and represents a new transition-metal-catalyzed oxidative cyclization of 1,6-enynes in a 6-exo-trig fashion.

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