Nucleophile-Controlled Regiodivergent Domino Reactions of Enetriones with γ-Bromocrotonates: Access to 1,3-Dienic Esters and Tetrasubstituted Pyrans
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 23, 2025
Herein,
we
developed
an
efficient
nucleophile-controlled
regiodivergent
domino
reaction
between
enetriones
and
γ-bromocrotonates.
This
method
allowed
for
the
rapid
synthesis
of
a
range
1,3-dienic
esters
tetrasubstituted
pyrans
under
metal-free
conditions.
In
presence
pyridine,
SN2
substitution/Michael
addition/elimination
sequence
formed
in
satisfactory
yields
with
high
E-stereoselectivities.
Alternatively,
addition/cyclization/cyclopropanation/cyclopropane
ring-opening
process
forged
good
help
Et3N.
It
is
interesting
to
note
that
site-selective
reactions
γ-bromocrotonates
at
α-
or
γ-position
were
readily
realized
by
modulating
pyridine
Furthermore,
simple
Et3N
act
as
both
nucleophiles
substitution
Lewis
bases
deprotonation
processes.
Язык: Английский
Base-Controlled Chemodivergent [4 + 1] and [2 + 1]/[4 + 2] Annulations of o-Aminochalcones with γ-Bromocrotonates
Organic Letters,
Год журнала:
2024,
Номер
26(43), С. 9203 - 9209
Опубликована: Окт. 21, 2024
Controlling
the
selectivity
of
reactions
is
a
significantly
attractive
strategy
in
synthetic
organic
chemistry.
Herein,
an
efficient
base-controlled
chemodivergent
domino
reaction
between
o-aminochalcones
and
γ-bromocrotonates
has
been
developed.
A
series
cis-2,3-disubstituted
indolines
cyclopropane-fused
tetrahydroquinolines
were
obtained
via
two
pathways
with
broad
substrate
scope
moderate
to
excellent
yields
under
transition-metal-free
conditions.
It
noteworthy
that
could
be
used
as
C1
or
C2
synthons
by
modulating
base;
particular,
both
nucleophiles
electrophiles
generate
cyclopropanes
for
first
time.
Язык: Английский