Chinese Journal of Chemistry,
Journal Year:
2022,
Volume and Issue:
40(13), P. 1608 - 1622
Published: April 3, 2022
Comprehensive
Summary
“Chain‐walking”
reactions
could
realize
to
modify
a
molecule
at
the
position
far
away
from
active
site.
It
has
been
hot
topic
in
research
field
of
organic
synthesis.
As
number
achievements
have
made
by
researchers,
products
transition
metal‐catalyzed
chain‐walking
be
obtained
with
good
enantioselectivity.
This
review
summarized
researches
on
asymmetric
catalyzed
metal
past
decade.
These
works
are
classified
according
species
catalysts.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(33)
Published: June 13, 2022
Abstract
Multi‐component
carbonylation
of
olefins,
a
reaction
that
installs
both
carbon–carbon(heteroatom)
bond
and
carbonyl
group
across
the
double
bond,
is
an
attractive
strategy
for
alkene
functionalization.
Herein,
we
developed
novel
nickel‐catalyzed
four‐component
olefins
with
ethers
under
low
CO
gas
pressure.
Using
alcohols
amines
as
partner,
diverse
γ
‐oxy‐substituted
esters
amides
were
produced
in
good
yields
excellent
functional
tolerance.
Notably,
Naftidrofuryl,
medicine
treatment
cerebrovascular
disease
(CVD),
can
be
synthesized
by
this
process
straightforwardly.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(46)
Published: Sept. 27, 2022
C-Acyl
glycosides
are
versatile
intermediates
to
natural
products
and
medicinally
relevant
entities.
Conventional
cross-coupling
strategies
secure
these
molecules
often
relied
on
two-component
manifolds
in
which
a
glycosyl
precursor
is
coupled
with
an
acyl
donor
(pre-synthesized
or
generated
situ)
under
transition
metal
dual
catalysis
forge
C-C
bond.
Here,
we
disclose
three-component
Ni-catalyzed
reductive
regime
that
facilitates
the
chemoselective
union
of
halides,
organoiodides
commercially
available
isobutyl
chloroformate
as
CO
surrogate.
The
method
tolerates
multiple
functionalities
resulting
obtained
high
diastereoselectivities.
Theoretical
calculations
provide
mechanistic
rationale
for
unexpectedly
chemoselectivity
sequential
cross-electrophile
couplings.
This
approach
enables
expeditious
assembly
difficult-to-synthesize
C-acyl
glycosides,
well
late-stage
keto-glycosylation
oligopeptides.
Journal of the American Chemical Society,
Journal Year:
2022,
Volume and Issue:
144(50), P. 23019 - 23029
Published: Dec. 8, 2022
The
reaction
of
common
acyl-metal
species
(acyl
anion)
with
aldehydes
to
furnish
acyloins
has
received
much
less
attention
and
specifically
was
restricted
using
preformed
stoichiometric
reagents.
Moreover,
the
(catalytic)
enantioselective
variants
remain
unexplored,
asymmetric
synthesis
chiral
met
significant
challenges
in
organic
synthesis.
Here,
we
uncover
highly
coupling
acid
chlorides
α-bromobenzoates
by
nickel
catalysis
for
producing
enantioenriched
protected
α-hydroxy
ketones
(acyloins,
>60
examples)
high
enantioselectivities
(up
99%
ee).
successful
execution
this
protocol
enables
formation
a
key
ketyl
radical
from
α-bromoalkyl
benzoate
situ
generated
corresponding
aldehyde
acyl
bromide,
which
finally
is
captured
acyl-Ni
catalytically
formed
chlorides,
thus
avoiding
use
synthetic
utility
chemistry
demonstrated
downstream
elaboration
toward
diverse
set
synthetically
valuable
building
blocks
biologically
active
compounds.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(14), P. 2699 - 2704
Published: April 7, 2022
Herein,
we
reported
a
Ni-catalyzed
carbonylation
of
cyclopropanol
with
benzyl
bromide
to
afford
multisubstituted
cyclopentenone
under
1
atm
CO.
The
reaction
proceeds
through
cascade
bromides,
followed
by
generation
nickel
homoenolate
from
cyclopropanols
via
β-C
elimination
1,4-diketones,
which
undergoes
intramolecular
Aldol
condensation
furnish
highly
substituted
derivatives
in
moderate
good
yields.
exhibits
high
functional
group
tolerance
broad
substrate
scope.
Chinese Journal of Chemistry,
Journal Year:
2022,
Volume and Issue:
40(13), P. 1608 - 1622
Published: April 3, 2022
Comprehensive
Summary
“Chain‐walking”
reactions
could
realize
to
modify
a
molecule
at
the
position
far
away
from
active
site.
It
has
been
hot
topic
in
research
field
of
organic
synthesis.
As
number
achievements
have
made
by
researchers,
products
transition
metal‐catalyzed
chain‐walking
be
obtained
with
good
enantioselectivity.
This
review
summarized
researches
on
asymmetric
catalyzed
metal
past
decade.
These
works
are
classified
according
species
catalysts.
