Chiral <i>N</i>,<i>N</i>′‑Dioxide Organocatalyzed Asymmetric Electrophilic α‑Cyanation of β‑Keto Esters and β‑Keto Amides

An enantioselective electrophilic α-cyanation of 1-indanone-derived β-keto esters and β-keto amides using a hypervalent iodine as the cyanide-transfer reagent was realized. A chiral <i>N</i>,<i>N</i>′-dioxide was used as the efficient bifunctional organocatalyst in the presence of inorganic base, which gave the corresponding α-cyano dicarbonyl compounds in yields of 50–99% with good enantioselectivities (87–97% ee)