10.1021/acs.orglett.6b00770.s001
Americo
J. Fraboni
Americo J.
Fraboni
Stacey E. Brenner-Moyer
Stacey E.
Brenner-Moyer
Dienamine-Catalyzed Nitrone Formation via Redox Reaction
American Chemical Society
2016
enal
accessing
heterocycle
Redox Reaction
nitrone functionality
aldehyde substrates
novel strategy
reactivity
Formation
method
dienamine catalysis
reaction proceeds
solvent
organocatalytic redox mechanism
Nitrone
equivalent
nitrosobenzene
2016-04-12 19:16:04
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Dienamine_Catalyzed_Nitrone_Formation_via_Redox_Reaction/3172420
The
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 <i>N</i>,<i>O</i>-heterocycles. Alternatively, divergent reactivity can
be suppressed simply by changing solvents.