Enantioselective Olefin Hydrocyanation without Cyanide

Asymmetric olefin hydrocyanation generally involves the formal addition of hydrogen cyanide across an alkene, through in situ generation or direct utilization of the highly toxic gaseous form. We have developed a dual CuH/Pd-catalyzed asymmetric cyanide-free olefin hydrocyanation process that relies on an oxazole as a nitrile equivalent. This method allowed for the formal asymmetric Markovnikov hydrocyanation of vinyl arenes and the anti-Markovnikov hydrocyanation of unactivated olefins.