Angewandte Chemie,
Год журнала:
2022,
Номер
134(37)
Опубликована: Июль 20, 2022
Abstract
1,1‐Diborylalkenes
can
be
transformed
into
(
Z
)‐skipped
dienes
through
Cu
I
‐phosphine
catalyzed
allylic
coupling
reactions.
The
energetically
preferred
formation
of
)‐α‐borylalkenyl
copper
(I)
species
and
the
subsequent
nucleophilic
attack,
explains
stereoselective
substitution
with
allyl
bromides.
eventual
treatment
NaO
t
Bu
promotes
cyclization/aromatization
patterns
via
enyne
intermediates.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 20, 2024
Abstract
The
stereoselective
cyclopropanation
of
olefins
with
“boron
ylide”
is
disclosed
for
the
first
time,
providing
a
modular
strategy
synthesis
stereospecific
diboryl‐functionalized
cyclopropanes.
chiral
gem
‐diborylcyclopropanes
are
synthesized
excellent
enantioselectivity
aid
auxiliary.
Based
on
powerful
transformable
ability
boryl
group,
those
challenging
multi‐quaternary
carbon
centers
in
cyclopropane
units
have
been
facilely
constructed
stereoselectivity.
Control
experiments
indicate
that
groups
necessary
both
chemoselectivity
and
stereoselectivity
control.
The Chemical Record,
Год журнала:
2024,
Номер
24(3)
Опубликована: Фев. 2, 2024
Abstract
The
wide
applications
of
alpha‐boryl
carbanions
in
selective
coupling
with
organohalides,
imines/carbonyls
and
conjugated
unsaturated
substrates
has
become
an
interesting
tool
for
organic
synthesis.
Strategically,
the
inclusion
heteroatoms,
such
as
Si,
S,
N,
F,
Cl,
Br
I
alpha
position
opens
a
new
venue
towards
multifunctionalities
molecular
design.
Here,
conceptual
practical
view
on
powerful
carbanions,
containing
α‐silicoboron,
α‐thioboron,
α‐haloboron
α‐aminoboron
is
given,
well
prespective
their
efficient
application
electrophilic
trapping.
A
modular
synthesis
method
for
1,4-diketones
has
been
developed.
Utilizing
inexpensive
carboxylic
acid
esters
as
carbonyl
sources
and
tetraborylethane
(TBE)
a
nucleophilic
reagent,
one-pot
strategy
constructing
two
C-C
bonds
was
established.
Notably,
this
reaction
proceeds
without
the
involvement
of
transition
metals
exhibits
excellent
functional
group
compatibility.
diverse
array
α-substituted
were
synthesized
using
various
electrophiles
capture.
Organic Letters,
Год журнала:
2022,
Номер
24(31), С. 5629 - 5634
Опубликована: Июль 29, 2022
An
enantioselective
(3+2)
cycloaddition
reaction
of
iminoesters
occurring
with
opposite
regioselectivity
is
reported.
This
provides
chiral
polysubstituted
pyrrolidines
high
enantioselectivities
(up
to
97%),
diastereoselectivities
(>20:1),
and
yields
99%).
Interestingly,
changing
the
alpha-substituents
from
an
aryl
aliphatic
(benzyl)
group
or
hydrogen
resulted
in
formation
normal
products,
also
excellent
enantioselectivities.
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
61(37)
Опубликована: Июль 20, 2022
1,1-Diborylalkenes
can
be
transformed
into
(Z)-skipped
dienes
through
CuI
-phosphine
catalyzed
allylic
coupling
reactions.
The
energetically
preferred
formation
of
(Z)-α-borylalkenyl
copper
(I)
species
and
the
subsequent
nucleophilic
attack,
explains
stereoselective
substitution
with
allyl
bromides.
eventual
treatment
NaOt
Bu
promotes
cyclization/aromatization
patterns
via
enyne
intermediates.
Angewandte Chemie,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 20, 2024
Abstract
The
stereoselective
cyclopropanation
of
olefins
with
“boron
ylide”
is
disclosed
for
the
first
time,
providing
a
modular
strategy
synthesis
stereospecific
diboryl‐functionalized
cyclopropanes.
chiral
gem
‐diborylcyclopropanes
are
synthesized
excellent
enantioselectivity
aid
auxiliary.
Based
on
powerful
transformable
ability
boryl
group,
those
challenging
multi‐quaternary
carbon
centers
in
cyclopropane
units
have
been
facilely
constructed
stereoselectivity.
Control
experiments
indicate
that
groups
necessary
both
chemoselectivity
and
stereoselectivity
control.
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(10), С. 1701 - 1707
Опубликована: Апрель 1, 2022
Abstract
We
describe
here
the
conjugate
addition
of
tert‐butyllithium
to
vinyl
systems
boronic
esters
generate
a
borata‐alkene
intermediate,
followed
by
sequential
S
N
2
reaction
with
alkyl
halides,
at
room
temperature.
envisioned
this
goal
through
engaged
C(
sp
3
)
chemical
entities
avoiding
metal
catalysts,
additives,
radical
initiators
or
specific
irradiation.
This
guarantees
that
new
tetrasubstituted
carbon
formed
retains
all
C
atoms
from
three
starting
materials
involved
in
assembly.
magnified
image
Organic Letters,
Год журнала:
2023,
Номер
25(29), С. 5492 - 5497
Опубликована: Июль 14, 2023
We
report
a
copper-catalyzed
asymmetric
reductive
coupling
of
vinyl
boronates
with
imines,
which
directly
access
enantiomerically
enriched
β-aminoalkylboronates.
Stereoselective
addition
the
in
situ
generated
chiral
α-borylalkyl
copper
to
N-phosphinoyl
imines
provided
target
products
good
yields
high
diastereo-
and
enantioselectivity.
Vinyl
boronate
methylated
acenaphthoquinone
as
boron
ligand
was
essential
efficiently
spawn
products,
organic
transformations
moiety,
along
easily
removable
N-protecting
group,
proved
their
synthetic
utility.
Chemical Synthesis,
Год журнала:
2021,
Номер
unknown
Опубликована: Янв. 1, 2021
Chemical
Synthesis
is
an
open
access
peer-reviewed
journal
publishing
original
research
involving
all
areas
of
the
chemical
sciences.
The
aims
to
be
premier
resource
seminal
and
insightful
showcases
for
researchers
in
both
academia
industry,
providing
a
platform
inspiration
future
chemistry.
intends
serve
as
preeminent
international
chemistry
has
ambition
among
first
choices
chemists
publication
their
discoveries.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(25), С. 5274 - 5280
Опубликована: Янв. 1, 2023
An
efficient
anti-Markovnikov
selective
transition
metal-
and
solvent-free
Lewis
base-mediated
protoboration
of
aromatic
aliphatic
alkenes
with
bis(pinacolato)diboron
(B2pin2)
as
the
boron
reagent
is
reported.
This
protocol
practical
demonstrates
broad
substrate
scope
good
functional-group
tolerance
on
to
give
synthetically
useful
alkyl
boronate
esters
in
excellent
yields
under
mild
reaction
conditions.
The
gram-scale
further
highlighted
usefulness
this
method.
