Computational assessment of non-heteroatom-stabilized carbene complexes reactivity: formation of oxazine derivatives.
A complete DFT-level mechanism elucidation of the two-step reaction of non-heteroatom-stabilized carbenes with imines, followed by addition of alkynes to yield oxazine derivatives, is presented. These compounds show different reactivity than the equivalent Fischer carbene complexes. A rationale of the experimental outcome is presented together with some suggestion for increasing the scope of the reaction, with special attention to the solvent effects in the regioselectivity.
Departamento de Química, Universidad de La Rioja , Centro de Investigación en Síntesis Química (CISQ), Madre de Dios, 51, 26006 Logroño, Spain.
Ignacio
I
Funes-Ardoiz
Diego
D
Sampedro