Isocyano Enones: Addition-Cyclization Cascade to Oxazoles.
Copper iodide catalyzes the conjugate addition of organometallic and heteroatom nucleophiles to isocyano enones to afford oxazoles. A range of enolates, metalated nitriles, amines, and thiols undergo catalyzed conjugate addition to cyclic and acyclic oxoalkene isocyanides. Mechanistic studies suggest that copper complexation facilitates the nucleophilic attack on the isocyano enone to generate an enolate that cyclizes onto the isocyanide leading to a variety of substituted acyclic or ring-fused oxazoles.
Department of Chemistry, Duquesne University , 600 Forbes Avenue, Pittsburgh, Pennsylvania 15282, United States.
Allen
A
Chao
Departmento de Química, Centro de Investigación y de Estudios Avanzados (Cinvestav) , Av Instituto Politécnico Nacional 2508, Ciudad de México 07360, México.
J Armando
JA
Lujan-Montelongo
Department of Chemistry, Drexel University , 32 South 32nd Street, Philadelphia, Pennsylvania 19104-2875, United States.
Fraser F
FF
Fleming
D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D007454:Iodides / Q000737:chemistry; D008314:Malonates / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis*
D003486:Cyanides; D007454:Iodides; D008314:Malonates; D010080:Oxazoles; D003300:Copper; C030290:malonic acid