4.8 Article

Dinuclear Zinc Catalyzed Asymmetric Spirannulation Reaction: An Umpolung Strategy for Formation of α-Alkylated-α-Hydroxyoxindoles

Journal

ORGANIC LETTERS
Volume 14, Issue 10, Pages 2446-2449

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol300577y

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Funding

  1. National Science Foundation
  2. Uehara Memorial Foundation
  3. JSPS
  4. Direct For Mathematical & Physical Scien
  5. Division Of Chemistry [0846427] Funding Source: National Science Foundation
  6. Direct For Mathematical & Physical Scien
  7. Division Of Chemistry [1145236] Funding Source: National Science Foundation

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A highly diastereo- and enantioselective formal [3 + 2] cycloaddition of alpha,beta-unsaturated esters and 3-hydroxyoxindoles catalyzed by a dinuclear zinc-ProPhenol complex is reported. The stereoselective Michael additions of 3-hydroxyoxindoles and the subsequent transesterifications afford spirocyclic delta-lactones.

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