4.8 Article

Rapid and Stereoselective Synthesis of Spirocyclic Ethers via the Intramolecular Piancatelli Rearrangement

Journal

ORGANIC LETTERS
Volume 15, Issue 3, Pages 476-479

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol303263q

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Funding

  1. UCSB
  2. National Science Foundation (CAREER Award) [CHE-1057180]
  3. Direct For Mathematical & Physical Scien
  4. Division Of Chemistry [1057180, 1040541] Funding Source: National Science Foundation

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The first example of a Piancatelli rearrangement of alcohols is demonstrated utilizing dysprosium(III) trif late as a catalyst to access oxaspirocycles in a highly diastereoselective manner. The cascade reaction constructs the spirocyclic ether ring system and the tertiary stereocenter in a single operation and is experimentally easy to perform.

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