ol6b00770_si_001.pdf (2.94 MB)
Dienamine-Catalyzed Nitrone Formation via Redox Reaction
journal contribution
posted on 2016-04-12, 19:16 authored by Americo
J. Fraboni, Stacey E. Brenner-MoyerThe
first catalytic method to directly introduce nitrone functionality
onto aldehyde substrates is described. This reaction proceeds by an
unprecedented organocatalytic redox mechanism in which an enal is
oxidized to the γ-nitrone via dienamine catalysis, thereby reducing
an equivalent of nitrosobenzene. This reaction is a unique example
of divergent reactivity of an enal, which represents a novel strategy
for rapidly accessing small libraries of N,O-heterocycles. Alternatively, divergent reactivity can
be suppressed simply by changing solvents.