4.8 Article

Synthesis of Spiroketals by Synergistic Gold and Scandium Catalysis

Journal

ORGANIC LETTERS
Volume 19, Issue 10, Pages 2526-2529

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00804

Keywords

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Funding

  1. Natural Science Foundation of China
  2. fundamental subject construction funds [104.205.2.5]
  3. Shandong University
  4. Shandong province [21572118, JQ201505]

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An ultrafast synthesis of spiroketals by synergistic gold(I) and Sc(III) catalysis has been reported. Diverse 5,6-benzannulated spiroketals were rapidly constructed by the diastereoselective [4 + 2] cycloaddition between gold-generated enol ether and Sc(III)-catalyzed o-quinone methide intermediates. Ultrafast reaction rate, ambient reaction temperature, general scope, high yields, excellent diastereoselectivity, and good scalability are attractive features of this method.

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