Cu(II)‐Catalyzed Enantioselective Aza‐Friedel‐Crafts Reaction of 1‐Naphthols and Electron‐Rich Phenols with Isatin‐Derived Ketimines
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(27)
Опубликована: Март 4, 2024
New
chiral
ligands
could
be
obtained
by
introducing
proline
moieties
and
imidazoline
to
binaphthyl
skeletons.
The
exhibited
balanced
rigidity
flexibility
which
allow
the
change
of
conformations
during
reactions
on
one
hand,
provide
sufficient
asymmetric
induction
other.
moiety
act
as
a
linker
connecting
skeletons
well
coordinating
group
for
central
metal,
electronic
steric
properties
groups
carefully
fine-tuned
use
different
substituents.
In
presence
Cu(II)
catalyst
bearing
such
ligands,
aza-Friedel-Crafts
reaction
1-naphthols
electron-rich
phenols
with
isatin-derived
ketimines
provided
desired
products
good
excellent
yields
up
99
%
ee.
showed
scalability,
ee
still
when
was
carried
out
in
gram-scale.
Язык: Английский
Baker’s yeast bio-catalyzed green and efficient synthesis of 3-indolylmethanamine via Aza-Friedel Crafts Reaction of indole with imines
Discover Chemistry.,
Год журнала:
2025,
Номер
2(1)
Опубликована: Апрель 16, 2025
Язык: Английский
Development and characterization of an aluminum-enhanced graphene oxide nanocomposite: An Eco-friendly and sustainable catalyst for electrochemical Friedel-crafts reactions
Journal of Molecular Structure,
Год журнала:
2024,
Номер
1319, С. 139373 - 139373
Опубликована: Июль 26, 2024
Язык: Английский
Copper(II)-Catalyzed Enantioselective Addition of Aryl Amines to Isatin-Derived N-Boc-Ketimines for the Synthesis of Acyclic N,N′-Ketals
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
90(1), С. 75 - 85
Опубликована: Дек. 31, 2024
Here,
we
demonstrated
a
copper(II)-catalyzed
enantioselective
addition
of
aryl
amines
to
isatin-derived
N-Boc-ketimines
using
chiral
O–N–N
tridentate
ligands
derived
from
BINOL
and
proline.
Generally,
the
acyclic
N,N′-ketals
were
obtained
in
high
yields
(up
98%)
excellent
ee
values
98%).
Various
could
be
tolerated
gram-scale
reaction
was
also
possible.
Further,
an
X-ray
diffraction
experiment
confirmed
that
configuration
N-Boc
ketimine
should
(Z).
Confirmation
would
make
it
easier
understand
rationale
for
stereofacial
selective
activation
electrophile
with
either
organo-
or
Lewis
acid–based
catalysts.
Язык: Английский