Organocatalytic Asymmetric Cyanosilylation of Nitroalkenes

Abstract

New catalyst, new reaction: The unprecedented cyanosilylation of nitroalkenes can be efficiently catalyzed by a bifunctional quinine derivative with tetraalkylammonium cyanide and thiourea moieties. The activation of the nitroalkene by hydrogen bonding to the thiourea, together with the presence of an “active” cyanide, provides a new mode of activation that leads to products in high yields and good selectivities (see scheme).