Asian Journal of Organic Chemistry,
Год журнала:
2023,
Номер
13(1)
Опубликована: Дек. 11, 2023
Abstract
This
study
reports
the
first
synthesis
of
tetrahydroquinaldic
and
tetrahydropicolinic
amides
using
readily
available
quinolines
pyridines
through
dearomative
difunctionalization
hydrolysis
under
transition‐metal‐
reductant‐free
conditions.
The
prepared
amide
products
could
be
easily
oxidized
to
corresponding
quinaldic
picolinic
amides.
Furthermore,
chemical
reactivity
group
has
been
explored
develop
convenient
methods
for
their
conversion
other
common
organic
functional
groups.
Angewandte Chemie,
Год журнала:
2023,
Номер
135(34)
Опубликована: Июль 3, 2023
Abstract
Herein,
we
report
a
one‐pot
method
for
enantioselective
C−H
allylation
of
pyridines
at
C3
via
tandem
borane
and
palladium
catalysis.
This
involves
borane‐catalyzed
pyridine
hydroboration
to
generate
dihydropyridines,
then
palladium‐catalyzed
the
dihydropyridines
with
allylic
esters,
finally
air
oxidation
allylated
afford
products.
enables
introduction
an
group
excellent
regio‐
enantioselectivities.
Angewandte Chemie,
Год журнала:
2023,
Номер
135(48)
Опубликована: Окт. 11, 2023
Abstract
A
copper‐catalyzed
dearomative
alkynylation
of
pyridines
is
reported
with
excellent
regio‐
and
enantioselectivities.
The
synthetically
valuable
enantioenriched
2‐alkynyl‐1,2‐dihydropyridine
products
afforded
are
generated
from
the
readily
available
feedstock,
pyridine,
commercially
terminal
alkynes.
three‐component
reaction
between
a
alkyne,
methyl
chloroformate
employs
copper
chloride
StackPhos,
chiral
biaryl
P
,
N‐
ligand,
as
catalytic
system.
Under
mild
conditions,
desired
1,2‐addition
delivered
in
up
to
99
%
yield
regioselectivity
ratios
25
:
1
enantioselectivities
values
ee.
Activated
non‐activated
alkynes
containing
wide
range
functional
groups
well
tolerated.
Even
acetylene
gas
mono‐alkynylated
high
Application
methodology
an
efficient
enantioselective
synthesis
piperidine
indolizidine,
coniceine,
reported.
Angewandte Chemie,
Год журнала:
2023,
Номер
135(49)
Опубликована: Окт. 20, 2023
Abstract
Nitrogen
heterocycles
play
a
vital
role
in
pharmaceuticals
and
natural
products,
with
the
six‐membered
aromatic
aliphatic
architectures
being
commonly
used.
While
synthetic
methods
for
N
‐heterocycles
are
well‐established,
synthesis
of
their
functionalized
analogues,
particularly
piperidine
derivatives,
poses
significant
challenge.
In
that
regard,
we
propose
stepwise
dearomative
functionalization
reaction
construction
highly
decorated
derivatives
diverse
functional
handles.
We
also
discuss
challenges
related
to
site‐selectivity,
regio‐
diastereoselectivity,
provide
insights
into
mechanism
through
mechanistic
studies
density
theory
computations.
Asian Journal of Organic Chemistry,
Год журнала:
2023,
Номер
13(1)
Опубликована: Дек. 11, 2023
Abstract
This
study
reports
the
first
synthesis
of
tetrahydroquinaldic
and
tetrahydropicolinic
amides
using
readily
available
quinolines
pyridines
through
dearomative
difunctionalization
hydrolysis
under
transition‐metal‐
reductant‐free
conditions.
The
prepared
amide
products
could
be
easily
oxidized
to
corresponding
quinaldic
picolinic
amides.
Furthermore,
chemical
reactivity
group
has
been
explored
develop
convenient
methods
for
their
conversion
other
common
organic
functional
groups.
