Angewandte Chemie,
Год журнала:
2023,
Номер
136(2)
Опубликована: Ноя. 28, 2023
Abstract
Allenoates
are
versatile
building
blocks
which
primarily
activated
and
controlled
using
chiral
tert.
phosphine
amine
Lewis
bases.
We
herein
report
the
first
example
of
allenoate
activation
by
isochalcogenoureas
(IChU)
for
formal
(4+2)
cycloaddition
reactions.
Compared
to
established
catalysis,
use
these
easily
available
bases
enables
new
stereoselective
reaction
pathways
proceeding
with
high
enantioselectivities,
diastereoselectivities,
in
good
yields.
In
addition,
factors
governing
enantioselectivity
origin
observed
differences
compared
other
commonly
used
explained.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(22), С. 4553 - 4573
Опубликована: Янв. 1, 2023
Compounds
featuring
aziridine
moieties
are
widely
known
and
extensively
reported
in
the
literature.
Due
to
their
great
potential
from
both
synthetic
pharmacological
points
of
view,
many
researchers
have
focused
efforts
on
development
new
methodologies
for
preparation
transformation
these
interesting
compounds.
Over
years,
more
ways
obtain
molecules
bearing
three-membered
functional
groups,
which
challenging
due
inherent
reactivity,
been
described.
Among
them,
several
sustainable.
In
this
review,
we
report
recent
advances
biological
chemical
evolution
derivatives,
particular,
variety
described
synthesis
aziridines
transformations
leading
formation
such
as
4-7
membered
heterocycles
pharmaceutical
interest
promising
activities.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
63(2)
Опубликована: Ноя. 28, 2023
Abstract
Allenoates
are
versatile
building
blocks
which
primarily
activated
and
controlled
using
chiral
tert.
phosphine
amine
Lewis
bases.
We
herein
report
the
first
example
of
allenoate
activation
by
isochalcogenoureas
(IChU)
for
formal
(4+2)
cycloaddition
reactions.
Compared
to
established
catalysis,
use
these
easily
available
bases
enables
new
stereoselective
reaction
pathways
proceeding
with
high
enantioselectivities,
diastereoselectivities,
in
good
yields.
In
addition,
factors
governing
enantioselectivity
origin
observed
differences
compared
other
commonly
used
explained.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(7), С. 1654 - 1660
Опубликована: Фев. 7, 2024
Abstract
Under
the
catalysis
of
a
Cu(I)
or
Ag(I)
salt
with
chiral
diphosphine
ligand,
enantioselective
nucleophilic
ring
opening
racemic
2‐styrenylaziridines
via
kinetic
resolution
dynamic
asymmetric
transformation
(DyKAT)
and
meso
aziridines
desymmetrization
alcohols
was
realized.
The
reaction
provided
range
vicinal
amino
ether
derivatives
in
47%‐98%
yields
50%–98%
ee.
could
be
extended
to
aliphatic
carboxylic
acids
as
nucleophiles.
synthetic
utility
demonstrated
four‐step
formal
synthesis
diastereomer
antirythmetic
agent
vernakalant.
Synthesis,
Год журнала:
2024,
Номер
56(22), С. 3365 - 3376
Опубликована: Апрель 15, 2024
Abstract
Vicinal
stereogenic
centers
represent
prevalent
structural
motifs
in
organic
synthetic
chemistry,
and
their
construction
poses
a
longstanding
challenge.
Transition-metal-catalyzed
asymmetric
allylic
substitution
has
become
well-established
enantioselective
C–C
bond-forming
reaction.
When
these
reactions
involve
prochiral
nucleophile
an
electrophile
with
terminal
substituent,
the
creation
of
vicinal
becomes
feasible.
However,
despite
remarkable
achievements
having
been
accomplished,
realizing
this
transformation
precise
control
over
both
enantio-
diastereoselectivity
remains
significant
To
address
stereoselective
challenges,
introduction
second
catalyst
to
transition-metal-catalyzed
alkylation
during
bond
formation
proven
particularly
fruitful.
In
short
review,
we
aim
highlight
recent
advances
dual
catalysis
that
enable
diastereo-
substitutions.
1
Introduction
2
Construction
Stereogenic
Centers
by
Organo
Metal
Dual
Catalysis
2.1
Chiral
Phase-Transfer
Transition-Metal
2.2
Amine
2.3
NHC
2.4
Aldehyde
2.5
Lewis
Base
3
3.1
Acidic
Iridium
3.2
Palladium
3.3
Ruthenium
3.4
Other
Advancements
through
Synergistic
Bimetallic
Enabling
Asymmetric
Allylic
Alkylation
4
Conclusions
Future
Outlook
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(39)
Опубликована: Авг. 25, 2023
We
herein
report
a
two-step
protocol
for
the
asymmetric
synthesis
of
novel
chiral
benzofused
ϵ-lactones
starting
from
O-protected
hydroxymethyl-para-quinone
methides
and
activated
aryl
esters.
By
using
isothiourea
Lewis
base
catalysts
broad
variety
differently
substituted
products
could
be
obtained
in
yields
around
50
%
over
both
steps
with
high
levels
enantioselectivities,
albeit
low
diastereoselectivities
only.
Synthesis,
Год журнала:
2024,
Номер
56(09), С. 1381 - 1392
Опубликована: Фев. 13, 2024
Abstract
A
highly
enantioselective
[4+2]
cyclization
of
azadienes
with
ketene
in
situ
generated
from
Pd-catalyzed
carbonylation
benzyl
bromides,
is
established
through
Pd/chiral
isothiourea
relay
catalysis.
The
key
this
transformation
the
formation
a
C1-ammonium
enolate
and
chiral
catalyst,
which
subsequently
undergoes
formal
reaction,
leading
to
3,4-dihydrobenzofuro[3,2-b]pyridine
derivatives
high
yields
excellent
levels
stereoselectivity.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(21), С. 4212 - 4242
Опубликована: Янв. 1, 2024
This
present
review
delineates
the
repertoire
of
vinyl
cyclopropanes
and
their
stuctural
analogues
to
accomplish
a
wide
array
oxa-cycles,
aza-cycles,
thia-cycles
under
transition
metal
catalysis
metal-free
approaches
from
early
2019
date.
The
generation
electrophilic
π-allyl
intermediates
1-3/1-5-dipolarophile
chemistry
originating
VCPs
are
always
green,
step-
atom-economical
sustainable
strategies
in
comparsion
with
prefunctionalized
and/or
C-H
activation
protocols.
Here,
strained
ring-system
extends
its
applicability
by
relieving
strain
undergo
ring-expansion
reaction
5-9
membered
carbo-
heterocyclic
systems.
availability
chiral
ligands
has
paved
way
realizing
asymmetric
synthetic
transformations.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(45)
Опубликована: Окт. 19, 2023
We
herein
report
a
two-step
approach
for
the
enantioselective
synthesis
of
novel
chiral
δ-lactams.
By
using
cooperative
ITU/achiral
Pd-catalyst
system,
this
protocol
proceeds
via
an
asymmetric
α-allylation
activated
aryl
esters
first,
followed
by
acid-mediated
lactam
formation.
A
variety
differently
substituted
products
could
be
obtained
with
usually
high
levels
enantioselectivities
and
in
reasonable
yields
(16
examples,
up
to
98
:
2
er
73
%
yield
over
two
steps).
In
addition,
further
utilizations
transformations
exocyclic
double
bond
were
successfully
carried
out
as
well.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(46), С. 9128 - 9132
Опубликована: Янв. 1, 2023
The
remarkable
biological
activities
of
γ-lactams
have
stimulated
the
search
for
efficient
synthetic
methods
to
achieve
these
scaffolds.
In
this
work,
we
developed
a
simple
one-pot
diastereoselective
synthesis
new
from
ketoaziridines
with
moderate
good
yields
via
Horner-Wadsworth-Emmons
reaction,
followed
by
an
intramolecular
ester-aziridine
cyclization
and
its
opening
in
situ.
Preliminary
efforts
towards
enantioselective
version
method
are
also
reported.
