Angewandte Chemie International Edition,
Journal Year:
2020,
Volume and Issue:
59(26), P. 10396 - 10400
Published: March 25, 2020
This
work
reports
gold-catalyzed
[4+3]-annulations
of
2-(1-alkynyl)-2-alken-1-ones
with
anthranils
to
yield
epoxybenzoazepine
products
excellent
exo-diastereoselectivity
(dr>25:1).
The
utility
this
new
gold
catalysis
is
manifested
by
applicable
substrates
over
a
broad
scope.
More
importantly,
the
enantioselective
versions
these
[4+3]-cycloadditions
have
been
developed
satisfactorily
chiral
catalysts
under
ambient
conditions
(DCM,
0
°C);
ee
levels
range
from
88.0-99.9
%.
With
DFT
calculations,
we
postulate
stepwise
pathway
rationalize
preferable
exo-stereoselection.
Chemical Society Reviews,
Journal Year:
2020,
Volume and Issue:
49(7), P. 2060 - 2118
Published: Jan. 1, 2020
This
review
article
provides
an
overview
of
progress
in
asymmetric
synthesis
allylic
compoundsviahydrofunctionalisation
and
difunctionalisation
dienes,
allenes,
alkynes.
Chemical Reviews,
Journal Year:
2020,
Volume and Issue:
121(14), P. 8613 - 8684
Published: Nov. 2, 2020
Three-
and
four-membered
rings,
widespread
motifs
in
nature
medicinal
chemistry,
have
fascinated
chemists
ever
since
their
discovery.
However,
due
to
energetic
considerations,
small
rings
are
often
difficult
assemble.
In
this
regard,
homogeneous
gold
catalysis
has
emerged
as
a
powerful
tool
construct
these
highly
strained
carbocycles.
This
review
aims
provide
comprehensive
summary
of
all
the
major
advances
discoveries
made
gold-catalyzed
synthesis
cyclopropanes,
cyclopropenes,
cyclobutanes,
cyclobutenes,
corresponding
heterocyclic
or
heterosubstituted
analogs.
Advanced Synthesis & Catalysis,
Journal Year:
2018,
Volume and Issue:
361(3), P. 405 - 425
Published: Aug. 20, 2018
Abstract
Fused
polycyclic
indoline
skeletons
are
found
in
many
natural
products
and
bioactive
molecules.
Several
approaches,
including
dearomative
cyclization
of
functionalized
indoles,
have
been
developed
for
the
rapid
synthesis
these
skeletons.
As
a
result
extensive
research
over
past
few
decades,
numerous
elegant
efficient
protocols
transition
metal‐catalyzed
indoles
to
afford
indolines
reported,
recent
developments
this
area
discussed
detail
review.
magnified
image
Advanced Materials,
Journal Year:
2020,
Volume and Issue:
32(41)
Published: March 17, 2020
Chirality
is
ubiquitous
in
nature
and
occurs
at
all
length
scales.
The
development
of
applications
for
chiral
nanostructures
rising
rapidly.
With
the
recent
achievements
atomically
precise
nanochemistry,
total
structures
ligand-protected
Au
other
metal
nanoclusters
(NCs)
are
successfully
obtained,
origins
chirality
discovered
to
be
associated
with
different
parts
cluster,
including
surface
ligands
(e.g.,
swirl
patterns),
organic-inorganic
interface
helical
stripes),
kernel.
Herein,
a
unified
picture
metal-ligand
bonding-induced
proposed.
bonding
modes
M-X
(where
M
=
X
binding
atom
ligand)
lead
on
nanoclusters,
which
turn
give
rise
various
characteristic
features
chirality.
A
comparison
Au-thiolate
NCs
Au-phosphine
ones
further
reveals
important
roles
bonding.
Compared
NCs,
Ag/Cu/Cd-thiolate
systems
exhibit
coordination
between
thiolate.
Other
than
thiolate
phosphine
ligands,
alkynyls
also
briefly
discussed.
Several
methods
obtaining
chiroptically
active
introduced,
such
as
enantioseparation
by
high-performance
liquid
chromatography
enantioselective
synthesis.
Future
perspectives
Chemistry - A European Journal,
Journal Year:
2019,
Volume and Issue:
26(7), P. 1442 - 1487
Published: Oct. 28, 2019
Abstract
Transition‐metal‐catalyzed
cross‐coupling
reactions
are
central
to
many
organic
synthesis
methodologies.
Traditionally,
Pd,
Ni,
Cu,
and
Fe
catalysts
used
promote
these
reactions.
Recently,
studies
have
showed
that
both
homogeneous
heterogeneous
Au
can
be
for
activating
selective
Here,
an
overview
of
the
past
studies,
current
trends,
future
directions
in
field
gold‐catalyzed
coupling
is
presented.
Design
strategies
accomplish
homocoupling
under
conditions,
computational
experimental
mechanistic
their
applications
diverse
fields
critically
reviewed.
Specific
topics
covered
are:
oxidant‐assisted
oxidant‐free
reactions;
strain‐assisted
dual
photoredox
catalysis;
bimetallic
synergistic
mechanisms
reductive
elimination
processes;
enzyme‐mimicking
chemistry;
cluster
surface
plasmonic
catalysis.
In
relevant
sections,
theoretical
I
/Au
III
chemistry
discussed
predictions
from
calculations
compared
with
observations
derive
useful
design
strategies.
ACS Catalysis,
Journal Year:
2020,
Volume and Issue:
10(18), P. 10672 - 10714
Published: Aug. 14, 2020
Enantioselective
transition
metal
catalysis
is
an
area
very
much
at
the
forefront
of
contemporary
synthetic
research.
The
development
processes
that
enable
efficient
synthesis
enantiopure
compounds
unquestionable
importance
to
chemists
working
within
many
diverse
fields
central
science.
Traditional
approaches
solving
this
challenge
have
typically
relied
on
leveraging
repulsive
steric
interactions
between
chiral
ligands
and
substrates
in
order
raise
energy
one
diastereomeric
states
over
other.
By
contrast,
Review
examines
alternative
tactic
which
a
set
attractive
noncovalent
operating
are
used
control
enantioselectivity.
Examples
where
creative
approach
has
been
successfully
applied
render
fundamental
enantioselective
presented
discussed.
In
cases
examined,
ligand
scaffold
carefully
designed
accommodate
these
interactions,
while
others,
critical
was
only
elucidated
subsequent
computational
mechanistic
studies.
Through
exploration
discussion
recent
reports
encompassing
wide
range
reaction
classes,
we
hope
inspire
continue
develop
asymmetric
transformations
based
powerful
concept.
Chemical Reviews,
Journal Year:
2021,
Volume and Issue:
121(14), P. 8311 - 8363
Published: Feb. 9, 2021
In
this
contribution,
we
provide
an
overview
of
the
main
avenues
that
have
emerged
in
gold
coordination
chemistry
during
last
years.
The
unique
properties
motivated
research
chemistry,
and
especially
regarding
applications
compounds
catalysis,
medicine,
materials
chemistry.
advances
synthesis
knowledge
been
possible
with
design
novel
ligands
becoming
relevant
motifs
allowed
preparation
elusive
complexes
area
research.
Strong
donor
easily
modulable
electronic
steric
properties,
such
as
stable
singlet
carbenes
or
cyclometalated
ligands,
decisive
stabilization
gold(0)
species,
fluoride
complexes,
hydrides,
unprecedented
π
cluster
derivatives.
These
new
important
not
only
from
fundamental
structure
bonding
studies
but
also
for
sophisticated
catalysts
to
improve
activity
selectivity
organic
transformations.
Moreover,
they
enabled
facile
oxidative
addition
gold(I)
gold(III)
a
plethora
specific
properties.
Journal of the American Chemical Society,
Journal Year:
2022,
Volume and Issue:
144(16), P. 7089 - 7095
Published: April 18, 2022
Presented
herein
is
the
first
report
of
enantioselective
Au(I)/Au(III)
redox
catalysis,
enabled
by
a
newly
designed
hemilabile
chiral
(P,N)-ligand
(ChetPhos).
The
potential
this
concept
has
been
demonstrated
development
1,2-oxyarylation
and
1,2-aminoarylation
alkenes
which
provided
direct
access
to
medicinally
relevant
3-oxy-
3-aminochromans
(up
88%
yield
99%
ee).
DFT
studies
were
carried
out
unravel
enantiodetermining
step,
revealed
that
stronger
trans
influence
phosphorus
allows
selective
positioning
substrate
in
C2-symmetric
environment
present
around
nitrogen,
imparting
high
level
enantioselectivity.
Angewandte Chemie International Edition,
Journal Year:
2017,
Volume and Issue:
56(50), P. 15905 - 15909
Published: Oct. 28, 2017
Abstract
Highly
enantioselective
gold‐catalyzed
intramolecular
cyclization
of
N‐allenamides
was
implemented
by
utilizing
a
designed
chiral
sulfinamide
phosphine
ligand
(PC‐Phos).
This
represents
the
first
example
highly
N‐allenamides.
The
practicality
this
reaction
validated
in
total
synthesis
(
R
)‐desbromoarborescidine
A
and
formal
C
)‐deplancheine.
Moreover,
catalyst
system
PC‐Phos/AuNTf
2
proved
to
be
specifically
efficient
promote
desymmetrization
excellent
yields
with
satisfactory
ee
values.
