Asymmetric Ring-Opening of Cyclopropyl Ketones with Thiol, Alcohol, and Carboxylic Acid Nucleophiles Catalyzed by a Chiral N,N′-Dioxide-Scandium(III) Complex

A highly efficient asymmetric ring-opening reaction of cyclopropyl ketones with a broad range of thiols, alcohols and carboxylic acids has been first realized by using a chiral N,N'-dioxide-scandium(III) complex as catalyst. The corresponding sulfides, ethers, and esters were obtained in up to 99% yield and 95% ee. This is also the first example of one catalytic system working for the ring-opening reaction of donor-acceptor cyclopropanes with three different nucleophiles, let alone in an asymmetric version.