European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
unknown
Опубликована: Ноя. 16, 2023
Abstract
Herein
we
report
the
first
synthesis
of
tetrahydrocarbazole
embedded
styrene
atropisomers
via
reaction
between
1‐(aryl‐ethynyl)‐naphthalen‐2‐ol
and
2,3,4,9‐tetrahydro‐1
H
‐carbazole.
The
proceeds
through
in
situ
vinylidene
ortho
‐quinone
methide
(VQM)
intermediate
formation.
derivatives
were
obtained
good
to
high
yields
with
diastereoselectivities
a
catalytic
amount
PTSA.
A
asymmetric
version
is
also
reported.
Chemical Society Reviews,
Год журнала:
2024,
Номер
53(22), С. 11165 - 11206
Опубликована: Янв. 1, 2024
This
review
explores
the
fascinating
world
of
molecules
featuring
multiple
stereogenic
elements,
unraveling
different
strategies
designed
over
years
for
their
enantioselective
synthesis.
The
asymmetric
catalytic
[3+2]
cycloannulation
of
benzoxazinones
with
isatin-derived
ketimines
for
the
efficient
construction
imidazo[5,1-c]oxazinones
has
been
developed,
which
realized
first
reaction
excellent
stereoselectivities.
A
series
containing
three
stereogenic
centers
one
gem-diamine-type
spiro
tetrasubstituted
center
were
obtained
in
this
organocatalytic
good
yields
and
high
functional
group
tolerance.
ACS Catalysis,
Год журнала:
2024,
Номер
14(17), С. 13055 - 13064
Опубликована: Авг. 15, 2024
Catalytic
asymmetric
hydrofunctionalization
of
π-bonds
has
been
extensively
studied,
but
the
alkynes
that
affords
atropoisometric
products
remains
heavily
underexplored.
We
herein
report
[Rh(COD)OAc]2/Mg(NTf2)2-catayzed
highly
atroposelective
hydroselenation
two
classes
1-alkynylindoles
using
selenophenols,
where
Mg(II)
salt
both
activates
Rh
catalyst
and
provides
a
key
NTf2
anion
essential
for
catalytic
activity
enantioselectivity,
affording
C–N
axially
chiral
trisubstituted
olefins
bear
relatively
low
racemization
barrier
(ΔG‡
∼
27
kcal/mol).
The
system
features
high
activity,
mild
reaction
conditions,
good
functional
group
tolerance,
regio-,
(E)-,
enantioselectivity.
selenoether
moiety
in
product
framework
can
be
readily
functionalized
to
give
synthetically
useful
products.
Synthesis,
Год журнала:
2023,
Номер
56(12), С. 1862 - 1872
Опубликована: Дек. 14, 2023
Abstract
The
construction
of
axially
chiral
alkene
frameworks
is
currently
one
hottest
topics
in
the
field
organic
synthetic
chemistry.
Compared
to
traditional
molecules,
such
as
biaryls,
heterobiaryls,
and
anilides,
synthesis
alkenes
far
more
challenging,
especially
for
acyclic
tetrasubstituted
analogues.
In
this
review,
we
summarized
development
strategies
analogues,
including
asymmetric
difunctionalization,
C–H
functionalization,
cross-coupling,
(dynamic)
kinetic
resolution,
allylic
substitution-isomerization.
1
Introduction
2
Synthesis
Cyclic
Tetrasubstituted
Axially
Chiral
Alkenes
3
Acyclic
4
Summary
Outlook
Organic Letters,
Год журнала:
2023,
Номер
25(37), С. 6913 - 6918
Опубликована: Сен. 11, 2023
Herein,
we
describe
a
stereoselective
sulfa-Michael/aldol
cyclization
reaction
promoted
by
rationally
designed
novel
axially
chiral
styrene-based
organocatalyst.
A
variety
of
highly
substituted
tetrahydrothiophenes
featuring
an
alkyne-substituted
quaternary
stereogenic
center
are
obtained
in
good
yields,
excellent
stereoselectivities,
and
exclusive
trans
selectivities.
This
process
tolerates
broad
range
alkynyl-substituted
acrylamides
under
mind
conditions.
The
utility
this
approach
is
highlighted
its
asymmetric
introduction,
scalability,
attractive
product
diversification.
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(34)
Опубликована: Апрель 16, 2024
Abstract
Here
we
report
B(C
6
F
5
)
3/
CPA‐catalyzed
enantioselective
aza‐Diels–Alder
reaction
of
3,3‐difluoro‐2‐Aryl‐3
H
‐indoles
with
unactivated
dienes
to
access
chiral
10,10‐difluoro‐tetrahydropyrido[1,2‐
a
]indoles.
This
protocol
allows
the
formation
pyrazole‐based
C2‐quaternary
indolin‐3‐ones
high
enantioselectivities
and
regioselectivities.
Moreover,
gram‐scale
synthesis
]indole
skeleton
was
successfully
achieved
without
any
reduction
in
both
yield
enantioselectivity.
Organic Letters,
Год журнала:
2024,
Номер
26(17), С. 3498 - 3502
Опубликована: Апрель 25, 2024
A
novel
ion
exchange
strategy
has
been
developed
to
enable
the
asymmetric
construction
of
axially
chiral
sulfone-containing
styrenes.
This
approach
provides
a
practical
synthesis
pathway
for
various
styrenes
with
good
yields,
exceptional
enantioselectivities,
and
nearly
complete
E/Z
selectivities.
Additionally,
reaction
mechanism
is
elucidated
in
detail
through
density
functional
theory
(DFT)
calculations.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(31)
Опубликована: Июнь 7, 2024
Abstract
Here,
we
have
successfully
achieved
the
addition
of
difluoroacetate
radicals
to
2‐aryl‐3
H
‐indol‐3‐ones,
enabling
various
difluoroalkylations
C2‐tetrasubstituted
2‐aryl
indolin‐3‐ones
in
a
highly
efficient
and
economical
manner.
It
is
worth
mentioning
that
these
difluoroalkylation
compounds
can
be
easily
transformed
into
derivatives
under
mild
reaction
conditions.
Control
experiments
suggest
involvement
ethyl
radical
species
reaction.
Organic Letters,
Год журнала:
2024,
Номер
26(27), С. 5657 - 5663
Опубликована: Июнь 28, 2024
A
protocol
for
the
electrooxidative
[3+2]
annulation
to
generate
indolo[2,3-b]indoles
in
an
undivided
cell
is
reported.
It
exhibits
good
yields
with
excellent
regioselectivities
and
tolerates
various
functional
groups
without
external
chemical
oxidants.
Cyclic
voltammetry
density
theory
calculations
indicate
that
initiated
by
simultaneous
anodic
oxidation
of
indole
aniline
derivatives,
step
determine
rate
relies
on
combination
radical
cations.
