Enantioselective Reductive Conjugate Alkenylation of α,β-Unsaturated Ketones and Amides via Nickel Catalysis
ACS Catalysis,
Год журнала:
2024,
Номер
14(8), С. 6228 - 6235
Опубликована: Апрель 10, 2024
Chiral
nickel
complexes
promoted
enantioselective
reductive
alkenylation
of
a
range
conjugated
enones,
using
alkenyl
bromides,
triflates,
and
tosylates.
The
neutral
condition
was
compatible
with
sensitive
groups
azaheteroaryl
rings.
Importantly,
in
products
can
be
readily
converted
to
functionalized
alkyl
via
iron-catalyzed
hydrofunctionalization.
Some
examples
asymmetric
N-enoyl
pyrroles
indoles
were
also
included.
Язык: Английский
Chiral phosphoric acid-catalyzed asymmetric epoxidation of alkenyl aza-heteroarenes using hydrogen peroxide
Nature Communications,
Год журнала:
2024,
Номер
15(1)
Опубликована: Июнь 20, 2024
The
synthesis
of
chiral
α-azaheteroaryl
oxiranes
via
enantioselective
catalysis
is
a
formidable
challenge
due
to
the
required
complex
stereoselectivity
and
diverse
N-heterocyclic
structures.
These
compounds
play
crucial
role
in
developing
bioactive
molecules,
where
precise
chirality
significantly
influences
biological
activity.
Here
we
show
that
using
phosphoric
acid
as
catalyst,
our
method
efficiently
addresses
these
challenges.
This
technique
not
only
achieves
high
enantio-
diastereoselectivity
but
also
demonstrates
superior
chemo-
stereocontrol
during
epoxidation
alkenyl
aza-heteroarenes.
Our
approach
leverages
synergistic
blend
electrostatic
hydrogen-bonding
interactions,
enabling
effective
activation
both
substrates
hydrogen
peroxide.
resulting
exhibit
enhanced
diversity
functionality,
aiding
construction
azaaryl
with
contiguous
stereocenters.
Kinetic
density
functional
theory
studies
elucidate
mechanism,
highlighting
acid's
pivotal
this
intricate
process.
Язык: Английский
α‐Azaaryl carbonyl derivatives in stereodivergent catalytic reactions
Bulletin of the Korean Chemical Society,
Год журнала:
2025,
Номер
unknown
Опубликована: Июнь 4, 2025
Abstract
The
catalytic
synthesis
of
chiral
azaarenes
has
become
a
focal
point
research
due
to
their
signifi`1cant
applications
across
various
fields,
including
medicinal
chemistry
and
materials
science.
α‐Azaaryl
carbonyl
compounds,
featuring
both
an
electron‐withdrawing
C=N
moiety
within
azaarene
core
functional
group,
have
proven
be
versatile
precursors
in
the
stereochemically
intricate
azaaryl
molecules.
In
particular,
generation
α‐azaaryl
enolate
intermediates,
catalyzed
by
Lewis
acids,
enabled
precise
construction
α‐stereogenic
azaarenes.
This
review
explores
recent
advances
stereodivergent
transformations
derivatives
with
array
carbon
electrophiles,
emphasizing
efficiency
systems
involving
copper
acids
combined
Ir,
Pd,
Ni,
amine,
or
Ru
catalysts.
These
strategies
offer
control
over
stereochemical
outcome,
facilitating
access
all
stereoisomers
multi‐stereogenic
Additionally,
we
discuss
sequence‐dependent
approach
that
allows
for
controlled
stereodivergence
reactions
derivatives.
Through
detailed
exploration
advancements,
mechanistic
insights,
practical
applications,
this
underscores
potential
unlock
new
avenues
compounds.
By
presenting
diverse
expanding
opportunities
controlling
stereochemistry,
it
fosters
further
development
design
structurally
complex
azaarene‐based
frameworks.
Язык: Английский
Enantioselective Synthesis of Chiral Organosilicon Compounds by Organocatalytic Asymmetric Conjugate Addition of Boronic Acids to β-Silyl-α,β-Unsaturated Ketones
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(5), С. 3254 - 3265
Опубликована: Фев. 22, 2023
Herein,
we
report
(R)-3,3′-(3,5-(CF3)2-C6H3)2-BINOL-catalyzed
enantioselective
conjugate
addition
of
organic
boronic
acids
to
β-silyl-α,β-unsaturated
ketones,
furnishing
moderate
excellent
yields
the
corresponding
β-silyl
carbonyl
compounds
with
stereogenic
centers
in
enantioselectivities
(up
98%
ee).
Moreover,
catalytic
system
features
mild
reaction
conditions,
high
efficiency,
broad
substrate
scope,
and
easy
scale-up.
Язык: Английский
Synthesis of warfarin analogs: conjugate addition reactions of alkenyl-substituted N-heterocycles with 4-hydroxycoumarin and related substrates
RSC Advances,
Год журнала:
2023,
Номер
13(7), С. 4754 - 4756
Опубликована: Янв. 1, 2023
We
have
developed
a
procedure
for
the
Michael
addition
of
4-hydroxycoumarins
to
vinyl-substituted
N-heterocycles.
The
chemistry
is
also
suitable
thiocoumarins
and
quinolinones.
A
mechanism
proposed
involving
nucleophilic
attack
at
vinyl-group
protonated
N-heterocycle.
Язык: Английский
Highly Enantioselective Chiral Diol-Catalyzed Conjugate Addition of Boronic Acids to α,β-Unsaturated Trifluoromethyl Ketones
Yajing Hou,
Lu Zhao,
Guo-Li Chai
и другие.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(24), С. 17461 - 17471
Опубликована: Ноя. 25, 2023
The
(R)-3,3′-(3,5-(CF3)2-C6H3)2-BINOL-catalyzed
enantioselective
conjugate
addition
of
organic
boronic
acids
to
α,β-unsaturated
1,1,1-trifluoromethyl
ketones
affords
corresponding
products
bearing
a
stereogenic
center
at
the
β-position
in
moderate
high
yields
and
excellent
enantioselectivities
(up
99%
ee),
without
any
1,2-addition
product
formation.
Moreover,
this
catalytic
protocol
features
mild
reaction
conditions,
broad
substrate
scope,
suitability
for
alkenylboronic
(hetero)arylboronic
acids,
easy
scale-up.
Язык: Английский
Olefins Hydrofunctionnalization; Hydroarylation (Vinylation, Alkynylation) of Electron Deficient Olefins
Elsevier eBooks,
Год журнала:
2023,
Номер
unknown, С. 2 - 29
Опубликована: Март 21, 2023
Язык: Английский
Chiral Binaphthol-Catalyzed Enantioselective Conjugate Addition of Alkenyl and Arylboronic Acids to α,β-Unsaturated Cyclic N-Sulfonyl Ketimines
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(18), С. 13137 - 13149
Опубликована: Сен. 3, 2024
The
chiral
binaphthol-catalyzed
enantioselective
conjugate
addition
of
alkenylboronic
acids
and
heteroarylboronic
to
cyclic
Язык: Английский