4.7 Article

Chiral N,N′-Dioxide Organocatalyzed Asymmetric Electrophilic α-Cyanation of β-Keto Esters and β-Keto Amides

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 1, Pages 701-708

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02726

Keywords

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Funding

  1. National Natural Science Foundation of China [21222206, 21332003, 21321061]
  2. Fok Ying Tung Education Foundation [141115]
  3. National Program for Support of Top-notch Young Professionals

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An enantioseledive electrophilic alpha-cyanation of 1-indanone-derived beta-keto esters and beta-keto amides using a hypervalent iodine as the cyanide-transfer reagent was realized. A. chiral N,N'-dioxide was as the efficient, bifunctional organocatalyst in the presence of inorganic base, which gave the corresponding alpha-cyano dicarbonyl compounds in yields of 50-99% with good enantioselectivities (87-97% ee).

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