ACS Catalysis,
Год журнала:
2024,
Номер
14(21), С. 16105 - 16114
Опубликована: Окт. 17, 2024
We
introduce
a
phosphine-catalyzed
cycloaddition
involving
unprecedented
long-range
intramolecular
proton
transfer,
facilitating
the
synthesis
of
nine-membered
heterocycles,
which
are
privileged
structures
in
natural
products,
as
well
potent
pharmacophores.
Experimental
and
computational
studies
revealed
that
enamide
tether
N-aromatic
zwitterion
directly
enables
regioselective
transfer
to
proceed
independently
outer-sphere
shuttling.
This
understanding
selective
has
led
improved
efficiency
regioselectivity
desired
1,9-proton
reaction
under
anhydrous
conditions,
thereby
advancing
development
higher-order
reactions.
Further
stereoselective
contraction
synthesized
cyclic
compounds
using
3-aza-Cope
rearrangement
demonstrates
synthetic
versatility
our
approach.
The
findings
this
study
not
only
advance
general
mechanism
but
also
broaden
its
practical
utility
various
chemical
fields.
Organic Letters,
Год журнала:
2023,
Номер
25(27), С. 5011 - 5016
Опубликована: Июнь 29, 2023
Ligand-directed
divergent
synthesis
(LDS)
is
an
important
synthetic
tool
for
the
preparation
of
structurally
diverse
organic
molecules
without
tedious
steps
to
modify
substrates.
Herein,
we
introduce
realization
3,4-,
1,2-,
and
1,4-cyclization
benzo[d]isothiazole-1,1-dioxide-fused
azadienes
(BDAs)
through
LDS,
leading
tetrahydro-2H-pyrans,
oxazinanes,
tetrahydro-2H-1,5-oxazocines,
respectively.
Using
phosphinooxazoline
(PHOX)
ligands,
have
developed
a
[4
+
2]
cycloaddition
between
BDAs
substituted
2-alkylidenetrimethylene
carbonates,
providing
access
multi-substituted
chiral
tetrahydro-2H-pyrans
in
good
yields
with
excellent
enantio-,
diastereo-,
regioselectivities.
Organic Letters,
Год журнала:
2023,
Номер
25(51), С. 9213 - 9218
Опубликована: Дек. 15, 2023
Herein
we
employed
ethynylethylene
carbonates
(EECs)
to
achieve
formal
[4
+
1]
and
[3
3]
cycloaddition
with
cyclic
1,3-dicarbonyl
compounds.
On
one
hand,
EECs
styryl
substitution
could
undergo
a
remotely
controlled
enantioselective
reaction.
This
reaction
exhibits
good
chemoselectivity,
regioselectivity,
enantioselectivity.
In
addition,
of
compounds
was
also
achieved,
leading
series
4H-pyrans
impressive
chemoselectivity
Organic Letters,
Год журнала:
2023,
Номер
25(30), С. 5624 - 5629
Опубликована: Июль 24, 2023
A
tandem
allylic
amination/oxa-Michael
addition
of
vinyl
methylene
cyclic
carbonates
(VMCCs)
has
been
developed
to
construct
heterocycles
by
single
palladium
catalysis
or
palladium-organo
relay
catalysis.
In
this
process,
the
bisnucleophiles
first
underwent
regioselective
amination,
and
then
second
nucleophilic
group
further
completed
hetero-Michael
reaction
form
a
series
heterocycles.
Among
them,
chiral
3,4-dihydro-2H-benzo[b][1,4]oxazines
could
be
produced
in
medium
high
yield
with
good
enantioselectivity
under
Chinese Journal of Chemistry,
Год журнала:
2023,
Номер
42(8), С. 829 - 834
Опубликована: Дек. 8, 2023
Comprehensive
Summary
The
Pd‐catalyzed
dipolar
cycloaddition
represents
a
significant
synthetic
strategy
for
the
construction
of
useful
heterocyclic
compounds.
This
study
developed
[4+2]
and
[6+2]
reactions
benzo[
d
]isothiazole
1,1‐dioxides
(BDs)
leading
to
synthesis
BD‐fused
1,3‐oxazinane
1,3‐oxazocane
derivatives,
respectively.
In
particular,
1,3‐oxazinanes
demonstrated
regio‐
enantioselective
characteristics,
resulting
in
products
with
good
yields,
enantioselectivity
regioselectivity
(if
applicable).
Furthermore,
reaction
this
work
represented
first
medium‐sized
ring
compounds
based
on
BDs.
Chemical Communications,
Год журнала:
2023,
Номер
59(97), С. 14467 - 14470
Опубликована: Янв. 1, 2023
The
construction
of
medium-sized
ring
compounds
has
been
a
prominent
research
area
in
synthetic
chemistry.
In
this
study,
we
developed
tandem
strategy
that
combines
allylic
amination
and
ring-opening
oxetanes
to
synthesize
heterocycles.
Specifically,
N-aryl
oxetan-3-amines
undergo
with
zwitterionic
π-allylpalladium,
followed
by
intramolecular
ring-opening,
resulting
the
formation
Notably,
are
able
achieve
synthesis
7-8
membered
heterocycles
moderate
good
yields
employing
different
types
π-allylpalladium
species.
Chemical Communications,
Год журнала:
2022,
Номер
58(95), С. 13258 - 13261
Опубликована: Янв. 1, 2022
An
efficient
cascade
approach
for
the
construction
of
nitrogen-containing
polycyclic
compounds
from
amines
tethered
with
an
alkenyl
(or
alkynyl)
group
and
divinyl
carbonates
is
described.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(10), С. 2864 - 2869
Опубликована: Янв. 1, 2024
A
novel
palladium-catalyzed
[4
+
4]
cycloaddition
of
2-pyrones
with
2-alkylidenetrimethylene
carbonates
has
been
developed
for
the
synthesis
bridged
eight-membered
oxygen
heterocycles
in
good
yields
and
excellent
stereoselectivities.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(40), С. 8162 - 8169
Опубликована: Янв. 1, 2023
The
zwitterionic
π-allylpalladium
species,
also
known
as
dipoles,
are
important
synthons
widely
used
in
various
reactions
including
cycloaddition
and
allylic
substitution.
This
study
reported
the
development
of
a
new
indole-fused
precursor
compound
its
application
[4
+
2]
substitution
reactions.
As
result,
synthesis
pyrrolo[3,2,1-ij]quinazolin-3-one
7-vinyl
indole
compounds
was
achieved
with
moderate
to
good
yields.
Notably,
reaction
exhibited
excellent
regio-
stereoselectivity.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(15), С. 4131 - 4137
Опубликована: Янв. 1, 2024
A
palladium-catalyzed
decarboxylative
(5
+
5)
cyclization
reaction
of
vinyloxazolidine-2,4-diones
for
the
synthesis
ten-membered
N,O-containing
heterocycles
is
disclosed.
