Nature Communications,
Год журнала:
2024,
Номер
15(1)
Опубликована: Фев. 17, 2024
α,α-Disubstituted
α-amino
acids
(α-AAs)
have
improved
properties
compared
to
other
types
of
amino
acids.
They
serve
as
modifiers
peptide
conformation
and
precursors
bioactive
compounds.
Therefore,
it
has
been
a
long-standing
goal
construct
this
highly
valuable
scaffold
efficiently
in
organic
synthesis
drug
discovery.
However,
access
α,α-disubstituted
α-AAs
is
challenging
largely
unexplored
due
their
steric
constraints.
To
overcome
these,
remarkable
advances
made
the
last
decades.
Emerging
strategies
such
synergistic
enantioselective
catalysis,
visible-light-mediated
photocatalysis,
metal-free
methodologies
CO
Chemical Reviews,
Год журнала:
2022,
Номер
122(15), С. 12544 - 12747
Опубликована: Июль 17, 2022
1,1,1,3,3,3-Hexafluoroisopropanol
(HFIP)
is
a
polar,
strongly
hydrogen
bond-donating
solvent
that
has
found
numerous
uses
in
organic
synthesis
due
to
its
ability
stabilize
ionic
species,
transfer
protons,
and
engage
range
of
other
intermolecular
interactions.
The
use
this
exponentially
increased
the
past
decade
become
choice
some
areas,
such
as
C–H
functionalization
chemistry.
In
review,
following
brief
history
HFIP
an
overview
physical
properties,
literature
examples
reactions
using
or
additive
are
presented,
emphasizing
effect
each
reaction.
Angewandte Chemie International Edition,
Год журнала:
2019,
Номер
58(35), С. 12190 - 12194
Опубликована: Июнь 28, 2019
Highly
enantioselective
[3+3]
and
[3+4]
annulations
of
isatin-derived
enals
with
ethynylethylene
carbonates
ethynyl
benzoxazinanones
are
enabled
by
NHC/cooper
cooperative
catalysis,
leading
to
a
big
library
spirooxindole
derivatives
in
high
structural
diversity
enantioselectivity
(up
99
%
ee).
Both
reactions
represent
nicely
synergistic
integration
NHC
copper
which
both
catalysts
activate
the
substrates
chiral
perfectly
controls
stereochemistry.
RSC Advances,
Год журнала:
2021,
Номер
11(16), С. 9130 - 9221
Опубликована: Янв. 1, 2021
This
review
provides
a
unique
and
comprehensive
overview
of
sodium
sulfinates
for
synthesizing
many
valuable
sulfur-containing
compounds,
such
as
thiosulfonates,
sulfonamides,
sulfides,
sulfones,
allyl
vinyl
sulfones
β-keto
sulfones.
ACS Catalysis,
Год журнала:
2021,
Номер
11(7), С. 4169 - 4204
Опубликована: Март 19, 2021
Arylsulfonyl
compounds
are
among
the
most
important
in
pharmaceutical
and
medicinal
chemistry.
Hence,
a
wide
variety
of
sulfonylation
methods
have
been
reported
recently.
This
review
summarizes
arylsulfonylation
methodologies
developed
last
5
years
includes
two
major
categories.
The
first
entails
direct
second
multicomponent
arylsulfonylation.
In
arylsulfonylation,
arylsulfonyl
reagents
react
with
C–H
activated
compounds,
alkynes,
alkenes
through
coupling
or
addition
reactions.
reactions,
arylation
various
substrates
sulfur
dioxide
surrogates,
such
as
DABSO,
Na2S2O5,
K2S2O5.
hydrazides,
aryl
boronic
acids,
silanes,
halides
widely
employed
that
surrogates
to
generate
an
source,
ensuing
reactions
proceed
via
pathways
analogous
those
ACS Catalysis,
Год журнала:
2024,
Номер
14(4), С. 2746 - 2757
Опубликована: Фев. 7, 2024
Remote
stereocontrol
in
transition-metal
catalysis
is
a
challenging
but
interesting
research
topic.
In
this
work,
we
achieved
copper-catalyzed
asymmetric
yne-allylic
substitution
using
electron-rich
arenes
and
acyclic
carbonates
through
remote
enantioselectivity
control.
The
reaction
delivers
variety
of
enantioenriched
products
that
contain
diverse
set
valuable
moieties,
such
as
conjugated
enynes,
indoles,
indolizines,
allenes,
dihydrofurans,
which
are
widely
used
organic
synthesis
act
key
units
bioactive
molecules
natural
products.
synthetic
value
protocol
has
been
demonstrated
series
further
transformations,
mechanistic
studies
have
conducted
to
gain
more
insight
into
the
reaction.
Journal of the American Chemical Society,
Год журнала:
2020,
Номер
142(37), С. 15860 - 15869
Опубликована: Авг. 19, 2020
Chiral
sulfones
are
important
structural
motifs
in
organic
synthesis
because
of
their
widespread
use
pharmaceutical
chemistry.
In
particular,
chiral
allylic
have
drawn
particular
interest
synthetic
utility.
However,
enantioselective
1,3-disubstituted
unsymmetrical
remains
a
challenge.
this
article,
we
report
protocol
for
(R)-DTBM-Segphos/Pd-catalyzed
regio-
and
hydrosulfonylation
1,3-dienes
with
sulfinic
acids,
which
provides
atom-
step-economical
access
to
sulfones.
The
reaction
occurs
under
mild
conditions
has
broad
substrate
scope.
Combined
experimental
computational
studies
suggest
that
the
is
initiated
by
ligand-to-ligand
hydrogen
transfer
followed
C–S
bond
reductive
elimination
via
six-membered
transition
state.
Steric
repulsion
between
olefinic
C–H
tert-butyl
group
(R)-DTBM-Segphos
was
found
be
key
factor
enantiocontrol.
Molecules,
Год журнала:
2019,
Номер
24(21), С. 3930 - 3930
Опубликована: Окт. 31, 2019
Functionalized
cyclic
organic
carbonates
and
carbamates
are
frequently
used
in
a
number
of
transition
metal-catalyzed
decarboxylative
reactions
for
the
construction
interesting
molecules.
These
transformations
have
attracted
more
research
attention
recent
years
mainly
due
to
their
advantages
less
waste
generation
versatile
reactivities.
On
basis
previous
reviews
on
this
hot
topic,
present
review
will
focus
development
functionalized
last
two
years.
Angewandte Chemie International Edition,
Год журнала:
2019,
Номер
59(3), С. 1340 - 1345
Опубликована: Сен. 10, 2019
Abstract
Chiral
sulfones
are
of
great
importance
in
medicinal
chemistry
and
chemical
synthesis.
Efficient
methods
for
preparing
enantiomerically
enriched
sulfone‐containing
molecules
can
therefore
be
significant
value;
such
methods,
however,
uncommon.
Herein,
we
report
the
first
general
palladium‐catalyzed
sulfonylation
vinyl
cyclic
carbonates
with
sodium
sulfinates.
A
series
tertiary
allylic
were
synthesized
good
yields
excellent
enantiomeric
ratios.
Both
aliphatic‐
aryl‐substituted
suitable
reactants
results.
This
reaction
features
broad
substrates
scope,
readily
available
starting
materials,
regio‐
enantioselectivity,
synthesis
sulfone‐bearing
quaternary
carbon
stereocenters.
Through
geranyl
derived
carbonate
1
h
,
achieve
formal
total
(+)‐agelasidine
A.
Angewandte Chemie International Edition,
Год журнала:
2020,
Номер
60(6), С. 2948 - 2951
Опубликована: Окт. 23, 2020
A
highly
enantio-
and
regioselective
hydrosulfonylation
of
1,3-dienes
with
sulfonyl
hydrazides
has
been
realized
by
using
a
palladium
catalyst
containing
monodentate
chiral
spiro
phosphoramidite
ligand.
The
reaction
provided
an
efficient
approach
to
synthetically
useful
allylic
sulfones.
Mechanistic
studies
suggest
that
the
proceeds
through
formation
allyl
hydrazine
intermediate
subsequent
rearrangement
sulfone
product.
transformation
product
is
enantioselectivity-determining
step.
