Lewis Acid-Catalyzed Asymmetric Selenocyanation of β‑Ketoesters with N‑Selenocyanatosaccharin

The first electrophilic asymmetric selenocyanation has been achieved in the presence of Ni­(OTf)2 and (R,R)-DBFOX/Ph using N-selenocyanatosaccharin as the new selenocyanation reagent. Thus, a series of α-selenocyanato-β-keto esters were synthesized with high yields (up to 99%) and good ee values (up to 92% ee). The readily preparation of the reagent and high enantioselectivity make this methodology much practical for the synthesis of chiral selenocyanates.