Isocyano Enones: Addition–Cyclization Cascade to Oxazoles

• DOI: 10.1021/acs.orglett.6b01147
• Publication Date: 2016-06-10T12:33:33Z
• Authors: Allen Chao; J. Armando Lujan-...; Fraser F. Fleming
• Keywords: Conjugate; Heteroatom; Chemoselectivity

Copper iodide catalyzes the conjugate addition of organometallic and heteroatom nucleophiles to isocyano enones afford oxazoles. A range enolates, metalated nitriles, amines, thiols undergo catalyzed cyclic acyclic oxoalkene isocyanides. Mechanistic studies suggest that copper complexation facilitates nucleophilic attack on enone generate an enolate cyclizes onto isocyanide leading a variety substituted or ring-fused