Catalytic Asymmetric Ring Opening Reactions of Vinylcyclopropanes
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(19)
Опубликована: Янв. 11, 2024
Abstract
Vinylcyclopropanes
(VCPs)
are
important
building
blocks
with
multifaceted
reactivity.
Catalytic
asymmetric
ring
opening
of
vinylcyclopropanes
is
a
highly
efficient
process
to
access
valuable
chiral
molecules
diverse
functionalities
that
can
be
further
functionalized
for
series
synthetic
purposes.
VCPs
very
well‐known
substrates
cycloaddition
reactions
and
this
chemistry
has
been
widely
explored.
On
the
contrary,
despite
enormous
potential,
development
new
innovative
strategies
catalytic,
somewhat
underdeveloped.
Recently,
several
significant
examples
have
emerged
in
literature
various
both
activated
unactivated
involve
transition
metal
catalysis.
These
developments
relevant
additions
vinylcyclopropane
chemistry.
In
review,
we
aim
summarize
all
catalytic
transformations
reported
till
date
provide
comprehensive
analysis
these
research
outcomes.
Язык: Английский
Electron Donor‐Acceptor (EDA) Complex Enabled C−C Cross‐Coupling Reactions of α‐Amino Radicals
Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
13(6)
Опубликована: Апрель 18, 2024
Abstract
Electron‐donor
acceptor
(EDA)
complex
has
been
an
integral
part
of
visible‐light
photocatalysis
and
is
different
from
the
traditional
photoredox
catalysis,
which
requires
exogenous
photocatalyst,
typically
a
colored
compound
to
initiate
photocatalytic
cycle.
Interestingly,
EDA‐complex
photochemistry
found
profound
use
in
activating
inert
α‐C−H
bonds
amines.
The
strategy
relied
upon
formation
between
donor
(amine)
(Lewis
acid),
harvesting
light
energy
perform
SET
process
generate
radical
cation
anion
intermediates.
then
loses
activated
acidic
proton
(because
SET,
acidity
α‐proton
increases
by
lowering
BDE)
form
α‐amino
radical,
participates
various
C−C
coupling
cascades.
In
this
review,
conceptual
approaches
for
generation
radicals
their
bond‐forming
reaction
under
triggered
will
be
discussed
with
particular
emphasis
on
mechanism
2018
onwards.
Язык: Английский
Asymmetric three-component Tsuji–Trost allylation reaction enabled by chiral aldehyde/palladium combined catalysis
Chemical Science,
Год журнала:
2024,
Номер
15(26), С. 10232 - 10236
Опубликована: Янв. 1, 2024
An
asymmetric
three-component
allylation
reaction
is
achieved
under
the
promotion
of
chiral
aldehyde/palladium
combined
catalysis
via
mixed
Heck/allylation
cascades.
Язык: Английский
Access to 5- to 14-Membered N-Heterocycles by Alkylamination of 1,3-Dienes via Palladium Catalysis
Guang‐Qiang Tan,
Qingqing Zhou,
Haitao Qin
и другие.
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 12, 2025
Medium-sized
rings
show
great
potential
in
medicinal
chemistry
but
are
difficult
to
achieve
via
direct
cyclization
reaction.
We
herein
report
a
versatile
and
mild
photocatalytic
approach
for
synthesis
of
medium-
large-sized
vinyl
N-heterocycles
by
radical-mediated
sulfonamides
with
pendant
1,3-dienes.
The
reaction
involves
the
generation
radicals
from
alkyl
halides
π-allylpalladium
species.
This
method
could
serve
as
platform
construction
Pd
catalysis.
Язык: Английский
Transition metal catalysed cascade C–C and C–O bond forming events of alkynes
Padmanava Barik,
Subhra Sriharsa Behera,
Laxmi Kanta Nayak
и другие.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(25), С. 5052 - 5086
Опубликована: Янв. 1, 2024
1,2/1,1-Difunctionalization
of
alkynes
(cascade
C–C
and
C–O
bond
formations)
serves
as
one
the
reliable
methods
for
synthesis
numerous
chemical
architectures.
Язык: Английский
New Avenues for the Synthesis of Oxa‐Cycles Using Lewis/Brønsted Acid mediated Carboxygenation and Carboalkoxylation of Alkynes
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(19)
Опубликована: Апрель 16, 2024
Abstract
The
cascade
functionalizations
of
alkynes
have
provided
many
elegant
methods
for
the
synthesis
useful
scaffolds.
Amongst
these
functionalizations,
ones
comprising
C−C
and
C−O
bond
formation
been
utilized
extensively
due
to
abundant
presence
oxygenated
motifs
in
various
bio‐active
natural
as
well
unnatural
products.
Transition‐metal
catalysis
is
a
mainstay
tandem
they
are
very
efficient.
However,
their
utilization
does
typically
involve
stoichiometric
additives
like
other
metal
salts
and/or
Lewis
acids/Brønsted
acids
(LA/BA).
Thus,
approaches
that
rely
solely
on
using
LA/BA,
make
vital
transformations
not
only
eco‐friendly
atom
economical
but
also
cost
beneficial
fast
emerging
complementary
alternatives.
present
review
addresses
gap
literature
by
summarizing
recent
developments
LA/BA
mediated
1,1/1,2‐carboxygenation
carboalkoxylation
oxa‐cycles.
reaction
mechanisms
particularly
emphasized
bring
out
understanding
needed
from
point
future
this
domain.
Язык: Английский
Highly Regio- and Diastereoselective Synthesis of 6,7-Dihydro-4H-furo[3,4-c]pyran Derivatives through Pd-Catalyzed Formal (3 + 3) Allylic Cycloaddition of 2-Butene-1,4-diols with 2-(1-Alkynyl)-2-alken-1-ones
Organic Letters,
Год журнала:
2024,
Номер
26(10), С. 2018 - 2022
Опубликована: Фев. 29, 2024
A
highly
efficient
synthesis
of
7-vinyl-6,7-dihydro-4H-furo[3,4-c]pyran
derivatives
from
2-butene-1,4-diols
and
2-(1-alkynyl)-2-alken-1-ones
has
been
achieved
with
high
regio-
diastereoselectivity
(dr
>
20:1)
by
Pd-catalyzed
tandem
heterocyclization/cross-coupling.
The
π-allyl
palladium
species
Int
II
generated
2-butene-1,4-diol
direct
cleavage
the
C–OH
bond
is
key
to
success
in
this
formal
(3
+
3)
cycloaddition
reaction.
Язык: Английский
Palladium-Catalyzed Cycloaddition Reactions of π–Allylpalladium 1,4-Dipoles with 1,3,5-Triazinanes: Access to Hexahydropyrimidines, 1,3-Oxazinanes, and 1,5-Diazocanes
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(12), С. 8363 - 8375
Опубликована: Июнь 7, 2024
Palladium-catalyzed
decarboxylation
of
5-methylene-1,3-oxazinan-2-ones
and
5-methylene-1,3-dioxan-2-ones
to
generate
aza-π-allylpalladium
oxa-π-allylpalladium
1,4-dipoles
for
[4
+
2]
cycloaddition
reaction
with
1,3,5-triazinanes
was
developed,
affording
a
wide
range
hexahydropyrimidine
1,3-oxazinane
derivatives
in
good
excellent
yields
(up
99%).
The
acyclic
sulfonamido-substituted
allylic
carbonates
as
1,4-dipole
precursors
also
apply
the
developed
synthesized
strategy,
achieving
synthesis
hexahydropyrimidines.
Moreover,
situ-generated
undergoing
dimeric
4]
were
demonstrated
by
construction
1,5-diazocane
derivatives.
Язык: Английский
Pd-Catalyzed Asymmetric Allylic Substitution Cascade via Desymmetrization for the Construction of Chiral Polyheterocycles
Pharmaceutical Fronts,
Год журнала:
2024,
Номер
06(03), С. e237 - e251
Опубликована: Авг. 6, 2024
Chiral
polyheterocycles
represent
an
important
class
of
compounds
because
their
prevalence
in
bioactive
natural
products
and
chiral
drugs.
Pd-catalyzed
allylic
substitution
is
a
powerful
synthetic
tool
for
forming
C–C
C–X
bonds
(X
=
N,
O,
S,
etc.).
Naturally,
asymmetric
cascade
reactions
that
utilize
are
undoubtedly
efficient
pathways
to
construct
heterocycles.
In
this
article,
we
reviewed
the
via
desymmetrization
meso-diol
diesters
cycloolefins,
construction
derivatives.
Язык: Английский
BF3.Et2O-Catalyzed/Mediated Alkyne Cyclization: A Comprehensive Review of Heterocycle Synthesis with Mechanistic Insights
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
The
advancements
in
heterocycle
synthesis
through
BF
3
·OEt
2
catalyzed/mediated
cyclization
of
alkynes
have
been
highlighted.
Язык: Английский