RSC Advances,
Год журнала:
2023,
Номер
13(51), С. 36293 - 36300
Опубликована: Янв. 1, 2023
An
exo-selective
Diels-Alder
(exo-DA)
reaction
in
which
the
formed
diastereomer
is
different
from
that
conventional
endo-selective
(endo-DA)
was
developed,
involves
a
dual-functional
Brønsted
acid
as
catalyst
and
not
only
dienophile
(vinylquinoline)
but
also
an
acyclic
diene
(dienylcarbamate)
having
sterically
less
demanding
substituent.
Factors
necessary
for
achieving
exo-DA
were
extracted
through
exhaustive
computational
search
of
corresponding
transition
states,
relative
orientation
firmly
defined
by
hydrogen
bonding
interactions
with
catalyst.
It
experimentally
verified
combined
use
catalyst,
such
phosphoric
acid,
conformationally
restricted
(dienylcarbamate),
realized
introduction
substituent
at
2-position
unit,
key
to
reaction.
A
catalytic
enantioselective
attempted
using
chiral
gave
rise
exo-adduct
fairly
good
enantioselectivity.
Organic Letters,
Год журнала:
2023,
Номер
25(8), С. 1336 - 1341
Опубликована: Фев. 23, 2023
A
concise
Fe-catalyzed
alkylazidation
of
α-trifluoromethylalkenes
via
a
C–C
bond
cleavage/radical
addition/azidation
cascade
is
described.
This
protocol
features
broad
substrate
scope,
excellent
functional
group
compatibility,
and
the
ability
to
be
performed
on
gram
scale,
thus
offering
practical
step-economic
approach
synthetically
useful
tertiary
α-trifluoromethyl
azides.
Organic Letters,
Год журнала:
2022,
Номер
24(43), С. 8088 - 8092
Опубликована: Окт. 24, 2022
The
first
enantioselective
hydrophosphonylation
of
ketimines
with
phosphine
oxides
was
developed.
reaction
unprotected
using
a
bis(imidazoline)-phosphoric
acid
catalyst
gave
chiral
α-quaternary
aminophosphorous
compounds
having
primary
amino
group
in
excellent
yields
and
enantioselectivities.
Based
on
experimental
results
DFT
calculation,
transition
states
were
proposed
to
explain
the
stereoselectivity
reaction.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(20), С. 5274 - 5283
Опубликована: Янв. 1, 2023
The
asymmetric
Friedel–Crafts
alkylation
of
3-bromo-3-substituted
oxindoles
with
arenes
and
heteroarenes
was
achieved
to
synthesize
enantioenriched
C3-arylated
oxindoles.
A
highly
enantioselective
Mn-catalyzed
hydrogenation
of
fluorinated
imines
has
been
realized.
The
success
this
is
attributed
to
the
use
chiral
ferrocenyl
P,N,N
ligand
bearing
an
additional
center
at
pyridinylmethyl
position.
displayed
broad
functional
group
tolerance,
thus
furnishing
a
wide
range
optically
active
amines
with
up
98%
enantiomeric
excess.
utility
methodology
well-demonstrated
by
scale-up
asymmetric
N-(4′-methoxyphenyl)-ethan-2,2,2-trifluoro-1-phenyl-1-imine.
Chemical Reviews,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 22, 2025
Fluorine
and
nitrogen
form
a
successful
partnership
in
organic
synthesis,
medicinal
chemistry,
material
sciences.
Although
fluorine-nitrogen
chemistry
has
long
rich
history,
this
field
received
increasing
interest
made
remarkable
progress
over
the
past
two
decades,
driven
by
recent
advancements
transition
metal
organocatalysis
photochemistry.
This
review,
emphasizing
contributions
from
2015
to
2023,
aims
update
state
of
art
synthesis
applications
nitrogen-based
organofluorine
functional
molecules
chemistry.
In
dedicated
sections,
we
first
focus
on
fluorine-containing
reagents
organized
according
type
groups
attached
nitrogen,
including
N-F,
N-RF,
N-SRF,
N-ORF.
review
also
covers
nitrogen-linked
building
blocks,
catalysts,
pharmaceuticals,
agrochemicals,
underlining
these
components'
broad
applicability
growing
importance
modern
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(45), С. 8849 - 8854
Опубликована: Янв. 1, 2022
Chiral
phosphoric
acid
catalyzed
enantioselective
addition
of
5-amino-isoxazoles
with
β,γ-alkynyl-α-ketimino
esters
provided
good
yields
and
excellent
enantioselectivities.
Beilstein Journal of Organic Chemistry,
Год журнала:
2023,
Номер
19, С. 956 - 981
Опубликована: Июнь 28, 2023
The
aza-Friedel–Crafts
reaction
allows
an
efficient
coupling
of
electron-rich
aromatic
systems
with
imines
for
the
facile
incorporation
aminoalkyl
groups
into
ring.
This
has
a
great
scope
forming
aza-stereocenters
which
can
be
tuned
by
different
asymmetric
catalysts.
review
assembles
recent
advances
in
reactions
mediated
organocatalysts.
mechanistic
interpretation
origin
stereoselectivity
is
also
explained.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(16), С. 3381 - 3387
Опубликована: Янв. 1, 2023
The
enantioselective
reaction
between
2,5-disubstituted
pyrroles
and
diaryl-ketimines,
generated
in
situ
from
isoindolinone-derived
alcohols,
is
described.
Pyrrole
derivatives
possessing
a
congested
tetrasubstituted
stereogenic
center
at
the
β-(C3)
position
are
generally
obtained
high
yields
enantioselectivities.
transformation
can
be
extended
to
2-monosubstituted
pyrroles,
generating
chiral
α-(C5)
functionalized
pyrrole
products.
Control
experiments
were
conducted
order
elucidate
origin
of
low
enantioselectivities
observed
some
