Advances in organocatalytic asymmetric [3 + 3] cycloadditions: synthesis of chiral six-membered (hetero)cyclic compounds
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(19), С. 5573 - 5604
Опубликована: Янв. 1, 2024
This
review
has
summarized
the
development
of
organocatalytic
asymmetric
[3
+
3]
cycloadditions
and
given
insights
into
remaining
challenges
to
promote
future
this
field.
Язык: Английский
Organocatalytic Enantioselective (4+2) Annulation of Cyclopropane Carbaldehydes with 2‐Mercapto‐1‐Arylethanones
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(5), С. 1113 - 1119
Опубликована: Янв. 23, 2024
Abstract
Here,
we
report
the
organocatalytic
enantioselective
synthesis
of
dihydrothiopyran
derivatives
from
trans
racemic
donor–acceptor
cyclopropane
carbaldehydes
(DACCs)
and
2‐mercapto‐1‐arylethanone
via
formal
thio
(4+2)
cycloaddition
involving
thia‐Michael
aldol
condensation
annulation.
Mechanistic
studies
indicate
a
typical
kinetic
resolution
(KR)
is
involved
in
this
transformation,
which
results
moderate
yields
enantiomeric
ratios.
Remarkably,
method
characterized
by
its
one‐pot
simplicity,
mild
reaction
conditions,
resilience
towards
air
moisture
interference.
Язык: Английский
Synthesis of Bridged Bicyclic Systems peri‐Annulated to the Indole Ring: Tropane‐Fused Indoles
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(12), С. 2784 - 2790
Опубликована: Апрель 23, 2024
Abstract
Ytterbium
triflate
catalysed
domino
reaction
of
(3‐formyl‐4‐indolyl)‐derived
donor‐acceptor
cyclopropane
with
primary
amines
provides
a
simple
approach
to
an
unprecedented
tetracyclic
skeleton
in
which
tropane
system
is
peri
‐annulated
indole
core.
This
process
involves
the
formation
imine
and
its
(3+2)‐cross‐cycloaddition
moiety,
yielding
tropane‐fused
core
under
mild
conditions.
These
products
are
significant
interest
for
pharmacology
as
potential
hybrid
molecules
dual
mode
action.
Язык: Английский
Water-mediated dipole transfer and deoxygenation of nitrones: Experimental and computational mechanistic insights
Journal of Molecular Structure,
Год журнала:
2025,
Номер
unknown, С. 141947 - 141947
Опубликована: Март 1, 2025
Язык: Английский
(3+2) Annulation of Donor–Acceptor Cyclopropanes with Difluoroenoxysilanes: Syntheses of gem-Difluorocyclopentenes via α,α-Difluoroketone Scaffolds
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 27, 2025
Herein,
we
present
an
acid-
and
base-mediated
approach
for
ring
opening
of
donor-acceptor
cyclopropanes
(DACs)
followed
by
(3+2)
annulation,
yielding
biologically
relevant
gem-difluorinated
cyclopentenes
via
α,α-difluoroketone
scaffolds.
Fluorinated
rings
are
essential
building
blocks
in
drug
discovery
materials
research.
This
methodology
has
a
broad
substrate
scope,
is
scalable,
provides
practical
synthetic
route
to
obtain
value-added
fluorinated
compounds.
Язык: Английский
Strain-Releasing Hydrogenation of Donor–Acceptor Cyclopropanes and Cyclobutanes via Electrochemical Site Selective Carbonyl Reduction
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 21, 2025
An
acid
or
hydrogen
gas-free
electrochemical
protocol
is
established
for
the
hydrogenation
of
strained
rings
(cyclopropane
and
cyclobutane)
at
room
temperature
atmospheric
pressure.
The
mechanistic
study
revealed
that
reaction
was
initiated
via
reduction
carbonyl
group.
methodology
highly
specific
toward
such
as
cyclopropane
cyclobutane,
which
exhibit
broad
functional
group
tolerance.
Язык: Английский
Ring-Opening of Donor-Acceptor Cyclopropane Diester for the Synthesis of Oxime Esters and 2,3-Dihydroazete Ester
Synthesis,
Год журнала:
2024,
Номер
57(01), С. 91 - 98
Опубликована: Май 29, 2024
Abstract
A
simple
and
efficient
approach
for
the
synthesis
of
privileged
oxime
esters
by
employing
donor-acceptor
cyclopropane
diesters
(DACs)
as
one
potential
precursors
is
reported.
The
strategy
involves
Lewis
acid
catalyzed
ring-opening
DACs,
resulting
in
an
open-chain
intermediate
followed
base-mediated
construction
corresponding
a
one-pot
reaction.
Moreover,
process
also
features
diethyl
4-(4-methoxyphenyl)azete-2,2(3H)-dicarboxylate.
Язык: Английский
DFT Study on the Mechanism of Phosphine-Catalyzed Ring-Opening Reaction of Cyclopropyl Ketone
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
In
the
present
study,
mechanism,
origin
of
chemoselectivity,
and
substituent
effects
phosphine-catalyzed
ring-opening
reaction
cyclopropyl
ketone
have
been
investigated
using
DFT
method.
Multiple
pathways,
including
formation
hydrofluorenone,
Cloke-Wilson
product,
cyclopenta-fused
were
studied
compared.
The
computational
results
show
that
pathway
for
hydrofluorenone
is
most
favorable
one,
which
involves
four
processes:
nucleophilic
substitution
to
open
three-membered
ring,
an
intramolecular
Michael
addition
enolate
intermediate,
[1,5]-proton
transfer
give
ylide,
Wittig
deliver
final
product.
For
disclosing
structural
analysis
local
reactivity
index
performed.
Moreover,
also
considered
QTAIM
analysis.
current
study
would
provide
useful
insights
understanding
chemoselective
reactions.
Язык: Английский