Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(19), P. 3241 - 3246
Published: July 31, 2023
Abstract
The
electrophilic
cyclization
via
the
boronate
complex
between
various
homoallylic
boronates
and
Selectfluor®
is
reported.
This
reaction
provides
a
fluoromethylated
cyclopropane
ring
that
was
difficult
to
synthesize
by
previous
methods.
use
of
phenyl
lithium,
which
activates
boronate,
important
for
reaction.
intermediate
species
in
this
observed
through
11
B{
1
H}
NMR
experiments.
We
also
demonstrate
synthesis
building
block,
including
fluoromethyl‐substituted
bioactive
compound.
Chemical Reviews,
Journal Year:
2024,
Volume and Issue:
124(5), P. 2441 - 2511
Published: Feb. 21, 2024
Boron-containing
compounds
(BCC)
have
emerged
as
important
pharmacophores.
To
date,
five
BCC
drugs
(including
boronic
acids
and
boroles)
been
approved
by
the
FDA
for
treatment
of
cancer,
infections,
atopic
dermatitis,
while
some
natural
are
included
in
dietary
supplements.
Boron's
Lewis
acidity
facilitates
a
mechanism
action
via
formation
reversible
covalent
bonds
within
active
site
target
proteins.
Boron
has
also
employed
development
fluorophores,
such
BODIPY
imaging,
carboranes
that
potential
neutron
capture
therapy
agents
well
novel
diagnostics
therapy.
The
utility
synthetic
become
multifaceted,
breadth
their
applications
continues
to
expand.
This
review
covers
many
uses
targets
boron
medicinal
chemistry.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(35)
Published: May 31, 2022
The
synthesis
of
molecules
bearing
two
or
more
contiguous,
quaternary
stereocenters
is
challenging,
owing
to
the
difficulty
in
controlling
stereochemistry
whilst
simultaneously
constructing
a
sterically
congested
motif.
Herein,
we
report
electrophile-induced
ring
contractive
1,2-metallate
rearrangement
6-membered
cyclic
alkenyl
boronate
complexes
for
cyclopentyl
boronic
esters
fully
substituted
with
high
levels
stereocontrol.
Remarkably,
simple
variation
reaction
solvent
enabled
their
diastereodivergent
construction
facile
access
complementary
diastereomeric
pairs.
utility
our
methodology
demonstrated
asymmetric
total
(+)-herbertene-1,14-diol.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(23), P. 3373 - 3382
Published: Jan. 1, 2023
This
article
summarizes
recent
efforts
in
developing
enantioselective
palladium-
and
nickel-catalyzed
ring-opening/coupling
reactions
of
cyclobutanones
with
a
tethered
aryl
halide.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(36)
Published: May 23, 2024
Bis(alkenyl)boronates
react
with
optically
active
Ir(π-allyl)
species
in
a
process
that
involves
allylation
of
the
more
substituted
olefin
and
1,2-metalate
shift
less
olefin.
The
method
constructs
valuable
enantioenriched
tertiary
allylic
boronic
esters
high
chemoselectivity,
enantioselectivity
diastereoselectivity.
Allylic
functionalization
reactions
transform
1,3-stereodiad
to
1,5-
1,6-stereochemical
relationships.
Chemical Science,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
Four-component
reactions
at
room
temperature
delivered
C–N
atropisomeric
peptide
analogues
possessing
both
central
and
axial
chirality
with
complete
diastereocontrol.
Reactions
elevated
selectively
afforded
the
other
diastereoisomer.
Journal of the American Chemical Society,
Journal Year:
2023,
Volume and Issue:
145(30), P. 16344 - 16349
Published: July 24, 2023
Synthesis
of
stereodefined
carbocyclic
and
heterocyclic
tertiary
boronic
esters
is
accomplished
by
performing
a
conjunctive
cross-coupling
reaction
on
preformed
cyclic
boron
ate
complexes.
Boronates
bearing
spirocyclic
aryl
bicyclic
skeletons
can
be
synthesized
enantioselectively
using
chiral
PHOX-ligated
Pd
catalyst
with
achiral
starting
material,
while
substrates
continuous
stereogenic
centers
generated
diastereoselectively.
A
variety
alkenyl
electrophiles
are
incorporated.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(16), P. 2928 - 2933
Published: April 18, 2023
α-Haloboronates
have
a
wide
range
of
applications
in
organic
chemistry
as
synthetic
synthons;
however,
traditional
methods
α-haloboronates
are
harsh
and
complicated.
Herein,
we
used
nBuLi
the
nucleophilic
reagent
to
attack
boron
atom
gem-diborylalkanes
form
tetracoordinate
species
successfully
achieved
α-chloroboronates
α-bromoboronates
with
readily
accessible
electrophilic
halogen
reagents
(NCS
NBS).
The
reaction
is
transition-metal-free
features
broad
substrate
scope
diversified
valuable
products.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(21), P. 5798 - 5801
Published: Jan. 1, 2022
A
palladium-catalyzed
enantioselective
domino
ring-opening/Hiyama
coupling
of
cyclobutanones
is
reported,
providing
chiral
1-indanones
bearing
a
versatile
alkenyl
group.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(16)
Published: Feb. 13, 2023
Alkenyl
boronate
complexes
react
with
acylated
quinolines
and
isoquinolines
via
1,2-metalate
rearrangement
to
give
alkylated,
dearomatized
heterocycles
in
good
yields,
diastereoselectivities,
regioselectivities.
This
multi-component
coupling
is
highly
modular
can
be
used
access
a
wide
scope
of
heterocyclic
scaffolds.
Chiral
boronic
esters
made
through
this
methodology
possess
high
synthetic
potential
transformed
into
various
functional
groups
one
step
without
racemization.
