Organic Letters,
Год журнала:
2024,
Номер
26(42), С. 9162 - 9167
Опубликована: Окт. 16, 2024
Herein,
we
describe
a
Cinchona-aminocatalyzed
enantioselective
α-hydrazination
of
an
α-formyl
amide
for
the
production
protected
quaternized
serines
as
tertiary
amides
with
ee's
generally
>98%
and
≤99%
yields.
The
proposed
TS
model
supported
by
density
functional
theory
calculations
involves
quinuclidinium
ion
Brønsted
acid-assisted
delivery
DtBAD,
which
occurs
from
Re
face
H-bonded
enaminone
when
using
9S-cinchonamine
catalyst,
resulting
in
hydrazide
R-configuration
determined
X-ray
analysis.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(19), С. 12895 - 12900
Опубликована: Май 2, 2024
A
nickel
complex
of
chiral
bisoxazolines
catalyzed
the
stereoselective
reductive
arylation
ketones
in
high
enantioselectivity.
range
common
acyclic
and
cyclic
reacted
without
aid
directing
groups.
Mechanistic
studies
using
isolated
a
bis(oxazoline)
(L)Ni(Ar)Br
revealed
that
Mn
reduction
was
not
needed,
while
Lewis
acidic
titanium
alkoxides
were
critical
to
ketone
insertion.
ACS Catalysis,
Год журнала:
2025,
Номер
15(3), С. 1487 - 1513
Опубликована: Янв. 9, 2025
Due
to
the
wide
applications
of
resulting
chiral
tertiary
homoallylic
alcohols
in
organic
synthesis,
catalytic
asymmetric
ketone
allylations
have
attracted
continuous
attention
from
synthetic
chemists.
Despite
inherent
difficulty
enantiofacial
differentiation
and
low
reactivity
ketones,
past
two
decades
witnessed
rapid
progress
allylation
ketones.
Many
efficient
methods
been
reported,
with
discovery
unprecedented
catalysts
reagents.
The
current
Review
aims
give
a
summary
achievements
this
area
2011
date
is
divided
into
six
parts
according
reagents
that
were
applied.
Special
paid
scope
application
each
method
brief
introduction
corresponding
mechanisms.
Chemical and Pharmaceutical Bulletin,
Год журнала:
2025,
Номер
73(6), С. 511 - 514
Опубликована: Июнь 5, 2025
Addressing
the
challenging
field
of
chemoenzymatic
dynamic
kinetic
resolution
(DKR)
tertiary
alcohols,
for
which
so
far
only
one
example
exists
in
literature,
we
combined
biocatalytic
esterification
and
oxovanadium-catalyzed
racemization,
operating
both
steps
two
different
compartments
reactor.
The
compartmentalization
heterogeneous
catalysts,
namely,
immobilized
lipase
A
from
Candida
antarctica
(CAL-A)
or
its
mutant
oxovanadium
species
on
mesoporous
silica,
was
achieved
using
a
polydimethylsiloxane
thimble,
avoiding
contact
with
water,
thus
maintaining
catalyst's
activity
thereby
successfully
improving
efficiency
DKR.
Utilizing
double
CAL-A
V278S
+
S429G,
ester
obtained
62%
yield
excellent
enantiomeric
excess
>99%
ee.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(18), С. 4516 - 4521
Опубликована: Янв. 1, 2023
Zinc-catalyzed
[5
+
1]
annulation
of
α-hydroxyl
aryl
ketones
with
cyclohexadienone-tethered
enones
has
been
developed,
giving
access
to
enantioenriched
bicyclic
pyran
scaffolds
bearing
two
oxa-quaternary
stereocenters.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(20), С. 2485 - 2498
Опубликована: Июнь 21, 2024
Comprehensive
Summary
The
construction
of
acyclic
quaternary
carbon
stereocenters,
which
are
ubiquitous
in
many
bioactive
compounds,
pharmaceuticals
and
natural
products,
has
been
a
long
persuit
synthetic
organic
chemistry.
Among
numerous
methods,
enantioselective
nickel‐catalysis
attracted
incremental
attention
recent
years.
This
review
summarizes
the
development
asymmetric
strategies,
research
progress,
mechanistic
investigations
for
generation
stereocenters
via
nickel
catalysis.
Key
Scientists
In
2006,
Zhou
group
RajanBabu
realized
nickel‐catalyzed
hydrovinylation
α‐substituted
styrenes
ethylene
to
construct
(QCSs)
by
using
spiro‐
binaphthyl
phosphoramidite
ligands,
respectively.
2016,
Watson
developed
Suzuki‐Miyaura
arylation
generate
QCSs
chirality
transfer
reaction.
2017,
Feng
Fu
conjugated/Michael
additions
build
QCSs,
2020,
Fang
made
first
success
hydrocyanation
alkenes
allenes.
2021,
Gregory
C.
co‐workers
disclosed
α‐functionalization
carbonyl
compounds
that
could
form
QCSs.
At
same
time,
Shi
constructed
chiral
functionalization
alkenes.
2023,
Kleij
applied
new
strategy
Ni‐catalyzed
regio‐
homoallylic
coupling
year,
Tao
demonstrated
novel
is
dinickel‐catalyzed
α‐alkylation
with
alkyl
iodides.
CrystEngComm,
Год журнала:
2024,
Номер
26(47), С. 6692 - 6700
Опубликована: Янв. 1, 2024
No
trend
was
detected
between
the
linker
length
and
catalytic
activity
of
bridged
copper(
ii
)-arylhydrazone
complexes
in
cyanosilylation
benzaldehyde
with
trimethylsilyl
cyanide.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(19), С. 4848 - 4853
Опубликована: Янв. 1, 2023
An
efficient
strategy
for
the
enantioselective
construction
of
spirodihydrofuran
oxindoles
with
vicinal
quaternary
stereocenters
was
first
developed
via
a
one-pot
Michael/iodization/S
N
2
nucleophilic
substitution
sequence.
Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
13(4)
Опубликована: Фев. 12, 2024
Abstract
Here,
we
reported
a
new
type
of
chiral
triazole‐oxazoline
ligands
for
enantiodivergent
catalysis.
These
feature
subtle
modifications
to
the
1,2,3‐triazole
skeleton
and
were
systematically
explored
in
context
palladium‐catalyzed
1,4‐addition
reactions
arylboronic
acid
cyclic
β‐substituted
enones.
The
introduction
specific
substituents
on
triazole
ligand
led
switchable
enantioselectivity,
accompanied
by
consistently
high
yields.
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(36)
Опубликована: Апрель 6, 2024
The
synthesis
of
enantiomerically
pure
tertiary
alcohols
is
an
important
issue
in
organic
a
range
pharmaceuticals
including
molecules
such
as
the
anti-HIV
drug
Efavirenz.
A
conceptually
elegant
approach
to
enantiomers
dynamic
kinetic
resolution
racemic
alcohols,
which,
however,
requires
efficient
racemization
strategies.
particularly
challenging
due
various
side
reactions
that
can
occur
because
their
high
tendency
for
elimination
reactions.
In
last
few
years,
several
complementary
catalytic
concepts
have
been
developed,
characterized
by
and
suppression
unwanted
side-reactions.
Besides
resins
bearing
sulfonic
acid
moieties
combination
boronic
oxalic
heterogeneous
homogeneous
Brønsted-acids,
respectively,
immobilized
oxovanadium
piperidine
turned
out
be
useful
catalysts.
latter
two
catalysts,
which
already
applied
different
types
substrates,
also
proven
good
compatibility
with
lipase,
thus
leading
first
examples
chemoenzymatic
alcohols.
this
review,
difficulties
racemizing
are
specifically
described,
recently
developed
overcome
these
hurdles
summarized.
