Organic & Biomolecular Chemistry,
Год журнала:
2018,
Номер
17(6), С. 1395 - 1401
Опубликована: Дек. 20, 2018
A
newly
developed
Ming-Phos
ligand
with
a
3,5-bis(trifluoromethyl)phenyl
substituent
was
demonstrated
to
be
highly
efficient
for
Ag-catalyzed
asymmetric
[3
+
2]
cycloaddition
reactions
of
azomethine
ylides
maleimides,
cyclopentene-1,3-diones,
and
N-(2-t-butylphenyl)maleimide.
Being
easily
prepared
on
the
gram
scale
in
one
step,
combination
Ag
catalyst
enables
synthesis
variety
functionalized
bicyclic
pyrrolidine
derivatives
good
yields
excellent
enantioselectivities
under
mild
conditions.
Organic Letters,
Год журнала:
2019,
Номер
21(3), С. 692 - 695
Опубликована: Янв. 11, 2019
With
the
synergistic
activation
of
alkynyl
alcohols
and
enones
by
a
single
gold
catalyst,
diverse
multisubstituted
spirocyclopenta[c]furans
were
synthesized
in
good
to
excellent
yields
under
mild
conditions.
Three
rings
constructed
efficiently
one
pot
from
easily
available
acyclic
starting
materials.
Journal of the American Chemical Society,
Год журнала:
2021,
Номер
143(43), С. 17983 - 17988
Опубликована: Окт. 26, 2021
Significant
attention
has
been
given
in
the
past
few
years
to
selective
transformations
of
N-tosylhydrazones
various
useful
compounds.
However,
development
enantioselective
versions
poses
considerable
challenges.
Herein
we
report
a
Pd-catalyzed
three-component
coupling
N-tosylhydrazone,
aryl
halide,
and
terminal
alkyne
under
mild
conditions
utilizing
novel
chiral
sulfinamide
phosphine
ligand
(GF-Phos),
which
provides
facile
access
diarylmethyl
alkynes,
are
synthons
organic
synthesis
as
well
exist
skeleton
many
bioactive
molecules.
A
pair
enantiomers
product
could
be
easily
prepared
using
same
by
simply
changing
substituents
N-tosylhydrazone
halide.
The
salient
features
this
reaction
include
readily
available
starting
materials,
general
substrate
scope,
high
enantioselectivity,
ease
scale-up,
conditions,
versatile
transformations.
Chinese Journal of Chemistry,
Год журнала:
2022,
Номер
40(12), С. 1407 - 1412
Опубликована: Фев. 23, 2022
Comprehensive
Summary
A
highly
enantioselective
gold‐catalyzed
intermolecular
[3
+
2]
cycloaddition
of
N
‐allenamides
with
nitrones
was
realized
by
the
application
Ming‐Phos
M6
as
a
chiral
ligand.
Both
enantiomers
cycloadducts
opposite
configuration
could
be
obtained
in
high
yields
regio‐
and
enantioselectivity
employment
either
diastereomer
The
acidic
N—H
bond
(hydrogen
bonding)
sulfinamide
moiety
pentaflurophenyl
substituent
(fluorine
effect)
may
play
important
roles
enhancement
enantioselectivity,
that
is,
is
multifunctional
ligand
this
transformation.
ACS Catalysis,
Год журнала:
2021,
Номер
12(1), С. 536 - 543
Опубликована: Дек. 20, 2021
A
one-pot
construction
of
bicyclo[3.2.1]oct-6-ene
frameworks
involves
gold-catalyzed
(4
+
3)-cycloadditions
between
2-(1-alkynyl)-2-alken-1-ones
and
substituted
cyclopentadienes;
diastereoselectivity
(dr
>25:1)
enantioselectivity
(up
to
99.9%
ee)
are
achieved
with
a
chiral
gold
catalyst.
Our
DFT
calculations
suggest
three-step
ionic
mechanism
for
the
cycloadditions
gold-containing
1,3-dipoles
cyclopentadienes,
in
which
an
exo-spatial
arrangement
is
preferable.
Israel Journal of Chemistry,
Год журнала:
2022,
Номер
63(9)
Опубликована: Авг. 29, 2022
Abstract
Gold
catalysis
has
emerged
as
an
efficient
tool
for
the
selective
functionalisation
of
C−C
multiple
bonds.
Despite
significant
progress
in
this
field,
potential
asymmetric
gold
not
been
fully
explored
to
date.
A
historical
retrospect
on
area
reveals
that
enantioselective
is
based
three
pillars:
Au(I)
catalysis,
Au(III)
and
Au(I)/Au(III)
redox
catalysis.
Irrespective
mode
being
operative,
design
new
ligands
crucial
development
gold‐catalysed
organic
transformations.
This
minireview
summarizes
made
ligand
focusing
which
were
specially
designed
Herein,
we
report
a
gold(I)-catalyzed
heterocyclization/(5
+
3)
cycloaddition
cascade
of
yne-enones
with
imidazolidines,
providing
modular,
atom-economical
and
efficient
strategy
for
the
synthesis
cycloocta[c]furans
in
moderate
to
excellent
yields.
This
method
features
readily
available
substrates,
simple
operation,
mild
reaction
conditions,
broad
substrate
scope.
More
importantly,
asymmetric
version
is
also
achieved
by
employing
(R)-C2-TunePhos
ligand
(L7),
leading
optically
active
up
98:2
er.
Organic Letters,
Год журнала:
2020,
Номер
22(9), С. 3551 - 3556
Опубликована: Апрель 14, 2020
A
highly
efficient
enantioselective
synthesis
of
multisubstituted
tetrahydrobenzofuran
derivatives
with
four
contiguous
stereocenters
was
established
by
the
dual
catalysis
a
gold(I)/chiral
N,N′-dioxide-cobalt(II)
complex
via
tandem
cycloisomerization/Diels–Alder
reaction
2-alkynyl-2-alkenones
and
electron-deficient
olefins.
This
strategy
not
only
featured
atom
economy,
remarkable
efficiency
stereoselectivity
but
also
highlighted
further
transformations
furan-based
products
into
polycyclic
molecules.
Moreover,
possible
transition-state
model
proposed
to
elucidate
origin
stereoselectivity.
Chinese Journal of Chemistry,
Год журнала:
2020,
Номер
38(6), С. 577 - 582
Опубликована: Фев. 26, 2020
Summary
of
main
observation
and
conclusion
A
gold(I)‐catalyzed
asymmetric
intermolecular
tandem
[3+3]‐cyclization
reaction
2‐(1‐alkynyl)‐2‐
alken‐1‐ones
with
nitrones
has
been
developed
by
using
Ming‐Phos
as
a
chiral
ligand.
This
method
enables
access
to
the
stereodivergent
synthesis
highly
substituted
furo[3,4‐
d
][1,2]oxazines
in
excellent
efficiency
stereoselectivity
(up
99%
yield,
ee
,
>20
:
1
dr).
Organic Letters,
Год журнала:
2021,
Номер
23(10), С. 4045 - 4050
Опубликована: Май 12, 2021
A
regiodivergent
nickel-catalyzed
hydrocyanation
of
1-aryl-4-silyl-1,3-diynes
is
reported.
When
appropriate
bisphosphine
and
phosphine–phosphite
ligands
are
applied,
the
same
starting
materials
can
be
converted
into
two
different
enynyl
nitriles
with
good
yields
high
regioselectivities.
The
DFT
calculations
unveiled
that
structural
features
bring
divergent
alkyne
insertion
modes,
which
in
turn
lead
to
Moreover,
synthetic
value
cyano-containing
1,3-enynes
has
been
demonstrated
several
downstream
transformations.
