Enantioselective Borylative Functionalization of Internal Alkenes: A Platform for Constructing Vicinal Stereocenters†
Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
42(24), P. 3588 - 3604
Published: Nov. 1, 2024
Comprehensive
Summary
Vicinal
stereogenic
centers
are
ubiquitous
structural
scaffolds
in
both
natural
products
and
synthetic
compounds,
yet
their
enantioselective
construction
remains
a
significant
challenge
organic
synthesis.
Organoboron
compounds
of
paramount
importance
chemistry
due
to
ability
undergo
facile
transformations,
yielding
diverse
essential
chemical
bonds
such
as
carbon‐carbon,
carbon‐oxygen,
carbon‐nitrogen,
carbon‐halogen
bonds.
Transition‐metal‐catalyzed
asymmetric
borylative
functionalizations
internal
alkenes
offer
promising
strategy
for
the
installation
two
adjacent
chiral
across
carbon‐carbon
By
leveraging
versatile
transformations
newly
introduced
boryl
unit,
this
approach
holds
great
potential
expanding
diversity
vicinal
scaffolds.
In
concise
review,
we
aim
highlight
recent
advancements
transition‐metal‐catalyzed
alkenes,
underscore
utility
constructing
centers,
discuss
unsolved
challenges
future
directions
field.
Key
Scientists
Language: Английский
Enantioselective Aminosilylation of Alkenes by Palladium/Ming‐Phos‐Catalyzed Tandem Narasaka–Heck/Silylation Reaction
Kangning Cao,
No information about this author
Jie Han,
No information about this author
Wenshao Ye
No information about this author
et al.
Advanced Science,
Journal Year:
2024,
Volume and Issue:
unknown
Published: July 5, 2024
A
Pd-catalyzed
enantioselective
aminosilylation
of
alkenes
via
tandem
Aza-Heck/silylation
reaction
under
Pd/Sadphos
catalysis
is
disclosed.
wide
array
oxime
esters
and
silicon
reagents
are
tolerated,
furnishing
the
chiral
pyrrolines
bearing
one
quaternary
or
two
contiguous
stereocenters
in
good
yield
with
high
enantioselectivity.
Not
only
terminal
but
also
tri-substituented
internal
successfully
participate
reaction,
delivering
vicinal
complete
diastereoselectivity
DFT
study
conducted
to
probe
pathway
origin
enantioselectivity,
which
revealed
that
stereoinduction
arises
from
weak
interaction
between
aromatic
ring
substrate
fragment
naphthyl
group
ligand.
Language: Английский
Enantioselective Copper-Catalyzed Three-Component Cascade Boronation–Dearomatization Reaction: Synthesis of Chiral Boron-Containing 1,4-Dihydropyridines
Fazhou Yang,
No information about this author
Yujie Dong,
No information about this author
Jinbao Wang
No information about this author
et al.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 10, 2025
A
three-component
cascade
boronation–dearomatization
reaction
of
alkenes,
a
diboron
compound,
and
pyridinium
salt
is
diclosed,
affording
chiral
boron-containing
1,4-dihyropyridines
in
high
yields
(≤98%)
diastereoselectivity
(≤10:1
dr),
along
with
excellent
enantioselectivity
(typically
>99%
ee).
The
catalytic
system
performs
efficiently
at
low
catalyst
loadings
(1
mol
%)
was
tested
>50
examples,
including
some
biologically
active
molecules.
Language: Английский
CuH-Catalyzed Regio- and Stereoselective Hydroalkoxylation of Styrenes with Acetal-Based Peroxides
Shōgo Nakamura,
No information about this author
Kyosuke Fujiwara,
No information about this author
Yuki Kojima
No information about this author
et al.
ACS Catalysis,
Journal Year:
2025,
Volume and Issue:
unknown, P. 8353 - 8360
Published: May 5, 2025
Language: Английский
Radical Arylboration of Unactivated Alkenes via Visible-Light Catalysis
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 7, 2025
A
photoinduced
radical
arylboration
of
unactivated
alkenes
with
B2pin2
and
aryl
nitriles
was
developed,
providing
a
mild
efficient
approach
to
access
useful
β-aryl
boronates
in
the
absence
transition-metal
catalyst.
This
reaction
undergoes
boron
addition
alkene
subsequent
radical-radical
coupling
process.
showcases
good
functional
group
compatibility
provides
promising
complementary
strategy
chemistry
traditional
transition-metal-catalyzed
coupling.
Language: Английский
Copper-catalyzed enantioselective three-component radical 1,4-perfluoroalkylamination of 1,3-dienes
Xiaoyan Shangguan,
No information about this author
Lihan Zhu,
No information about this author
Y.‐W. ZHANG
No information about this author
et al.
Nature Communications,
Journal Year:
2025,
Volume and Issue:
16(1)
Published: May 28, 2025
Language: Английский
Enantio- and E-Selective Copper-Catalyzed Three-Component Hydrofunctionalization of Internal Allenes Bearing Methylidenecyclobutanes with Diborons and Ketones
Yujie Dong,
No information about this author
Nianci Zhang,
No information about this author
Rongjin Ning
No information about this author
et al.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: June 5, 2025
Internal
allenes
are
challenging
substrates
in
copper-catalyzed
borylative
difunctionalization.
When
internal
featuring
a
methylidenecyclobutane
motif
were
employed,
hydrofunctionalization
reaction
using
diborons
and
ketones
as
partners
the
presence
of
chiral
monophosphorus
ligand
was
developed,
affording
series
unsaturated
tertiary
alcohols
preserving
high
regio-
stereoselectivities.
Control
experiments
suggest
that
involves
boronation-deboronation
process,
plausible
mechanism
has
been
proposed.
Language: Английский
Synthesis of axially chiral thiourea by NHC-catalyzed desymmetrizative amidation
Yingtao Wu,
No information about this author
Xin Guan,
No information about this author
Kehan Jiao
No information about this author
et al.
Green Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
NHC-catalyzed
desymmetrization
amidation
of
biaryl
dialdehydes
has
been
developed
for
NH-free
axially
chiral
thiourea.
Sequential
kinetic
resolution
enhances
the
chirality
induction
strategy,
expanding
applicable
scope.
Language: Английский
Olefination of Activated Alkyl Halides with Phosphonium Salts
Synthesis,
Journal Year:
2024,
Volume and Issue:
56(24), P. 3923 - 3928
Published: Nov. 7, 2024
Abstract
A
base-promoted
olefination
reaction
between
alkylphosphonium
salts
and
activated
alkyl
halides
has
been
developed.
The
products
were
obtained
in
excellent
E-selectivity.
In
contrast
to
most
other
reactions
of
phosphonium
salts,
the
yields
triphenylphosphine
as
main
by-product,
which
can
be
directly
reused
formation
new
salts.
Language: Английский