4.8 Article

Gold-Catalyzed Cascade Friedel-Crafts/Furan-Alkyne Cycloisomerizations for the Highly Efficient Synthesis of Arylated (Z)-Enones or -Enals

Journal

ORGANIC LETTERS
Volume 11, Issue 17, Pages 3838-3841

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol901408u

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Funding

  1. National Natural Science Foundation of China [20872163, 20732008, 20821002]
  2. Chinese Academy of Science
  3. Science and Technology Commission of Shanghai Municipality
  4. Major State Basic Research Development Program [2006CB806105]

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An efficient domino approach for the synthesis of arylated (Z)-enones or -enals through gold(I)-catalyzed reactions of enynols with furans was developed. PPh3AuNTf2 was found to be an excellent catalyst to catalyze both of the Friedel-Crafts and furan/alkyne cyclization reactions in the same vessel. This method offers several advantages such as high stereoselectivities, mild reaction conditions, and easily accessible starting materials.

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