Design of rigid chiral bipyridine-2NO tetradentate ligands: application in asymmetric catalysis
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(5), С. 1314 - 1321
Опубликована: Янв. 1, 2024
A
new
class
of
chiral
bipyridine-2NO
ligands,
which
incorporate
the
advantages
both
bipyridine
skeleton
and
pyrroloimidazolone-based
N
-oxide
moiety,
was
developed.
Язык: Английский
Bipyridine-N,N′-dioxides Catalysts: Design, Synthesis, and Application in Asymmetric Synthesis of 1H-Pyrazolo[3,4-b]pyridine Analogues
Organic Letters,
Год журнала:
2024,
Номер
26(17), С. 3487 - 3492
Опубликована: Апрель 18, 2024
A
novel
type
of
highly
efficient
chiral
C2-symmetric
bipyridine-N,N′-dioxides
ligand
application
in
catalyzing
Michael
addition/Cyclization
5-aminopyrazoles
with
α,β-unsaturated
2-acyl
imidazoles
has
been
developed,
affording
the
corresponding
adducts
85–97%
yield
up
to
99%
enantioselectivity
under
mild
conditions
a
lower
catalyst
loading
and
broad
scope.
Remarkably,
this
protocol
exhibits
advantages
terms
reactivity
enantioselectivity,
giving
fact
that
as
low
2.2
mol
%
L1
2.0
Ni(OTf)2
can
promote
title
reaction
on
gram
scale
afford
desired
product
excellent
enantioselectivity.
Язык: Английский
Py-2NO ligand enabled Ni(ii)-catalyzed asymmetric Michael addition reaction of indoles with β,γ-unsaturated α-keto esters
New Journal of Chemistry,
Год журнала:
2024,
Номер
48(4), С. 1688 - 1695
Опубликована: Янв. 1, 2024
This
work
diversified
the
Py-2NO
ligand
library
recently
developed
by
our
group
and
further
expanded
application
of
chiral
ligands
in
asymmetric
catalysis.
Язык: Английский
Chiral Phenol‐2NO Ligand Cooperation with Achiral Organic Base in the Zn(II)‐Catalyzed Asymmetric Alkylation Reaction of Indoles
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(13), С. 1474 - 1480
Опубликована: Март 1, 2024
Comprehensive
Summary
The
privileged
C
2
‐symmetric
rigid
phenol‐type
ligand
is
more
attractive
but
challenging
in
asymmetric
catalysis.
Herein,
we
designed
and
synthesized
a
class
of
rigid‐featured
chiral
tridentate
Phenol‐2NO
ligands,
that
incorporate
the
advantages
both
phenol
skeleton
pyrroloimidazolone‐based
N
‐oxide
moiety,
from
readily
available
L
‐prolinamides
operationally
simple
two
steps
up
to
44%
overall
yield.
More
importantly,
using
an
achiral
quinoline
derivative
as
additive,
newly
developed
could
serve
anioic
upon
deprotonative
activation
coordinate
Zn(II)
form
highly
enantioselective
catalyst
for
Michael‐type
Friedel‐Crafts
alkylation
reaction
indoles
with
2,3‐dioxopyrrolidines.
Excellent
yields
(up
90%)
high
enantioselectivities
99%
ee)
are
obtained
wide
range
substrates
under
mild
conditions.
Experiments
DFT
calculations
revealed
mechanism
origins
enantioselectivity.
This
also
represented
first
ligand/metal
complex
by
organic
base
additive
Язык: Английский
Phen-2NO, a new C2-symmetric rigid-featured tetradentate ligand, and its application in the asymmetric alkylation reaction of indoles
New Journal of Chemistry,
Год журнала:
2024,
Номер
48(15), С. 6670 - 6675
Опубликована: Янв. 1, 2024
A
new
class
of
C
2
-symmetric
rigid-featured
chiral
phen
ligands
that
provide
the
N
,
O
-tetradentate
coordination
moiety
and
two
additional
-dioxides
were
rationally
designed
developed.
Язык: Английский
Naphthyridine–2NO, a new C2-symmetric rigid tetradentate bimetallic ligand and its application in asymmetric Friedel–Crafts alkylation
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(9), С. 2600 - 2606
Опубликована: Янв. 1, 2024
The
development
of
a
series
novel
and
easily
accessed
chiral
naphthyridine-type
binucleating
ligands
for
asymmetric
catalysis.
Язык: Английский
Modular Synthesis of C2‐Symmetric Chiral TPy‐BPI Pincer Ligands and Application in Asymmetric Ni(II)‐Catalysed Friedel‐Crafts Alkylation
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 17, 2024
Comprehensive
Summary
Terpyridine
ligands
have
been
applied
as
a
class
of
unique
due
to
their
rich
coordination
chemistry
in
the
catalysis.
Herein,
we
developed
new
C
2
‐symmetric
chiral
terpyridine‐pyrroloimidazolone
(TPy‐BPI).
Their
catalytic
activity
was
evaluated
asymmetric
Friedel‐Crafts
alkylation
indoles
with
2,3‐dioxopyrrolidines.
Excellent
yields
(up
92%)
and
high
enantioselectivities
97%
ee)
are
obtained
for
wide
range
substrates
under
mild
conditions.
In
addition
2,3‐dioxopyrrolidines,
β
,
γ
‐unsaturated
α
‐ketoesters
were
also
compatible
Ni(OTf)
‐TPy‐BPI
ligand
L1
‐catalyzed
reaction.
Control
experiments,
single
crystal
structure
two
TPy‐BPI
‐Ni(OTf)
complexes,
DFT
calculations
revealed
origins
enantioselectivity.
To
best
our
knowledge,
work
is
first
report
showing
that
terpyridine
framework
contained
only
nitrogen
atoms
coordinating
metal,
additional
pyridine
unit
acted
stereodirecting
element,
which
different
from
previously
reported
containing
all
three
metal.
Язык: Английский