4.8 Article

[3+2] Coupling of Quinone Monoacetals by Combined Acid-Hydrogen Bond Donor

Journal

ORGANIC LETTERS
Volume 13, Issue 18, Pages 4814-4817

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol201886r

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Funding

  1. Japan Society for the Promotion of Science (JSPS)
  2. Ritsumeikan Global Innovation Research Organization (R-GIRO)
  3. Asahi Glass Foundation
  4. Grants-in-Aid for Scientific Research [21249002] Funding Source: KAKEN

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The expeditious and efficient [3 + 2] coupling approach of quinone monoacetals 1 with alkene nucleophiles 2 by the action of an activated Bronsted acid in the presence of a hydrogen bond donor perfluorinated alcohol has been achieved. With the optimized combined acid, the reaction could proceed under mild conditions by only mixing the two reactants to afford the cycloadducts 3 in a short time (within 10 min) with good to quantitative yields.

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