4.8 Article

Gold-Catalyzed 1,2-Acyloxy Migration/Intramolecular [3+2] 1,3-Dipolar Cycloaddtion Cascade Reaction: An Efficient Strategy for Syntheses of Medium-Sized-Ring Ethers and Amines

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 40, Pages 10789-10793

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406486

Keywords

cycloaddition; gold; heterocycles; medium-ring compounds; synthetic methods

Funding

  1. Fundamental Research Funds for the MOST [2010CB833200]
  2. NSFC [21125207, 21372103, 21102062, 21203080]
  3. SRFDP [20130211110018]

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A highly efficient strategy for the formation of medium-sized-ring ethers and amines based on a gold-catalyzed cascade reaction, involving enynyl ester isomerization and intramolecular [3+2] cyclization, has been developed. Various multisubstituted medium-sized-ring unsaturated ethers and amines were obtained through this transformation. This method represents one of the relatively few transition metal catalyzed intramolecular cycloaddition reactions for medium-sized ring synthesis.

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