Angewandte Chemie,
Journal Year:
2020,
Volume and Issue:
132(42), P. 18610 - 18614
Published: July 8, 2020
Abstract
Herein,
we
report
that
highly
chemoselective
and
enantioselective
reduction
of
2‐vinyl‐substituted
pyridines
has
been
achieved
for
the
first
time.
The
reaction,
which
uses
chiral
spiro‐bicyclic
bisboranes
as
catalysts
HBpin
an
acidic
amide
reducing
reagents,
proceeds
through
a
cascade
process
involving
1,4‐hydroboration
followed
by
transfer
hydrogenation
dihydropyridine
intermediate.
retained
double
bond
in
products
permits
their
conversion
to
natural
other
useful
heterocyclic
compounds
simple
transformations.
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.
Angewandte Chemie International Edition,
Journal Year:
2021,
Volume and Issue:
60(52), P. 27288 - 27292
Published: Sept. 28, 2021
Abstract
A
Pd‐catalyzed
hydrophosphinylation
of
alkyl
and
aryl‐oxyallenes
with
phosphine
oxides
has
been
developed
for
the
efficient
rapid
construction
a
family
chiral
allylic
diverse
range
functional
groups.
This
methodology
was
further
applied
in
facile
2
H
‐chromene
later
stage
functionalization
cholesterol.
Journal of the American Chemical Society,
Journal Year:
2022,
Volume and Issue:
144(25), P. 11364 - 11376
Published: June 10, 2022
Pd-catalyzed
sequential
hydroamination
of
readily
available
1,3-enynes
is
reported.
The
redox-neutral
process
provides
an
efficient
route
to
synthesize
a
broad
scope
imidazolidinones,
thiadiazolidines,
and
imidazolidines.
Asymmetric
generates
series
synthetically
valuable,
enantioenriched
imidazolidinones.
Mechanistic
studies
revealed
that
the
transformation
occurred
via
intermolecular
enyne
pathway
give
allene
intermediate.
Subsequent
intramolecular
intermediate
proceeded
under
Curtin-Hammett
principle
provide
imidazolidinone
products.
Journal of the American Chemical Society,
Journal Year:
2021,
Volume and Issue:
143(18), P. 6724 - 6745
Published: April 23, 2021
Tandem
catalysis
enables
the
rapid
construction
of
complex
architectures
from
simple
building
blocks.
This
Perspective
shares
our
interest
in
combining
stereoselective
hydrogenation
with
transformations
such
as
isomerization,
oxidation,
and
epimerization
to
solve
diverse
challenges.
We
highlight
use
tandem
for
preparing
natural
products
prochiral
blocks
present
involving
transfer
dynamic
kinetic
resolution.
Finally,
we
underline
recent
breakthroughs
opportunities
asymmetric
hydrogenation.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(25), P. 16996 - 17002
Published: June 14, 2024
A
highly
regio-
and
enantioselective
hydrosulfonylation
using
commercially
available
sodium
sulfinates
is
reported,
providing
the
first
direct
asymmetric
rhodium-catalyzed
of
allenes/alkynes
to
synthesize
chiral
allylic
sulfones.
Ligand
screening
studies
demonstrated
indispensable
role
C1-symmetric
P,N-ligand
(Rax,S,S)-StackPhim
for
achieving
both
high
regioselecitivity
(>20:1)
enantioselectivity
(up
97%
ee).
Notably,
operationally
simple
method
mild
conditions
allow
rapid
preparation
sulfones
with
a
wide
scope
functional
groups.
Moreover,
use
tert-butyldimethylsilyloxymethanesulfinate
enables
collective
synthesis
various
sulfone
derivatives
after
transformations
protected
hydroxymethyl
product.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(23), P. 16248 - 16256
Published: May 29, 2024
The
development
of
chiral
hydrogen
donor
catalysts
is
fundamental
in
the
expansion
and
innovation
asymmetric
organocatalyzed
reactions
via
an
enantioselective
atom
transfer
(HAT)
process.
Herein,
unprecedented
type
C2-symmetric
arylthiol
derived
from
readily
available
enantiomeric
lactate
ester
was
developed.
With
these
catalysts,
anti-Markovnikov
alkene
hydroamination–cyclization
reaction
established,
affording
a
variety
pharmaceutically
interesting
3-substituted
piperidines
with
moderate
to
high
enantioselectivity.
Results
designed
control
experiments
theoretical
computation
rationalized
origin
stereocontrol
disclosed
spatial
effect
moiety
thiols
on
We
believed
facile
synthesis,
flexible
tunability,
effective
enantioselectivity-controlling
capability
would
shed
light
versatile
HAT
related
reactions.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(29), P. 5407 - 5411
Published: July 18, 2022
Herein,
a
photoinduced
palladium-catalyzed
annulation
of
1,3-dienes
with
bifunctional
halognated
alkylamines
has
been
developed,
offering
facile
route
to
access
broad
range
vinylpyrrolidines.
The
reactivity
profile
this
protocol
was
able
be
readily
manipulated
assemble
vinylpyrrolidine
and
vinlysilaazacycle.
Remarkably,
the
utility
strategy
further
illustrated
in
construction
complex
biologically
important
molecules
as
well
diversity-oriented
transformations
resulting
product.
Accounts of Chemical Research,
Journal Year:
2023,
Volume and Issue:
56(24), P. 3676 - 3693
Published: Dec. 8, 2023
ConspectusFinding
efficient
synthetic
methods
for
the
asymmetric
synthesis
of
complex
molecules
has
always
been
interest
to
organic
chemists.
Creating
and
controlling
stereochemistry
stereogenic
centers
bearing
branched
allylic
moieties
in
using
a
catalytic
process
is
an
attractive
successful
method
several
natural
products
medicinally
important
compounds.
Remarkable
progress
toward
their
achieved
via
transition-metal
catalysis,
especially
case
substitution
C-H
oxidation
chemistry.
However,
preinstallation
leaving
group
essential,
oxidation,
stoichiometric
amounts
oxidant
are
required.
Besides
that,
control
regioselectivity
with
these
often
problematic
because
linear
product
can
be
produced
as
major
isomer.
Our
research
developed
regioselective,
enantioselective,
atom
economic
route
more
valuable
Rh-catalyzed
coupling
easily
accessible
alkynes
or
double-bond
isomeric
allenes
pronucleophiles.
It
was
demonstrated
this
new
approach,
it
possible
add
different
pronucleophiles
form
through
C-C
C-heteroatom
bond
formation.
Since
reactions
offer
opportunities
chemical
benchmark
application
target-oriented
synthesis,
we
have
syntheses
relevant
targets.
For
example,
total
Quercuslactones,
Helicascolides
A-C,
Epothilone
D,
Homolargazole,
Thailandepsin
B,
hydro-oxycarbonylation
used
key
step
C-O
Remarkably,
C2-symmetric
dimerization
strategy
synthesize
Clavosolide
A
Vermiculine,
leading
extreme
increase
structural
complexity
within
single
step.
Centrolobine,
Pitavastatin,
Rosuvastatin,
formation
addition
hydroxy
function
allene
moiety.
The
potential
nitrogen
Cusparein,
Angusterein,
Cermicin
C,
Senepodin
G,
Homoproline,
Pipecolinol,
Coniceine,
Coniine,
Ruxolitinib,
Sitagliptin,
Abacavir,
Glucokinase
activators,
Chaetominine.
All
examples
testify
wide
applicability
Account
summarize
our
contribution.
Angewandte Chemie International Edition,
Journal Year:
2020,
Volume and Issue:
59(42), P. 18452 - 18456
Published: July 8, 2020
Abstract
Herein,
we
report
that
highly
chemoselective
and
enantioselective
reduction
of
2‐vinyl‐substituted
pyridines
has
been
achieved
for
the
first
time.
The
reaction,
which
uses
chiral
spiro‐bicyclic
bisboranes
as
catalysts
HBpin
an
acidic
amide
reducing
reagents,
proceeds
through
a
cascade
process
involving
1,4‐hydroboration
followed
by
transfer
hydrogenation
dihydropyridine
intermediate.
retained
double
bond
in
products
permits
their
conversion
to
natural
other
useful
heterocyclic
compounds
simple
transformations.
