Synthesis,
Год журнала:
2024,
Номер
56(24), С. 3870 - 3878
Опубликована: Окт. 7, 2024
Abstract
The
development
of
new
catalytic
systems
that
enable
regio-
and
chemoselective
construction
diversely
functionalized
oxazocines
is
an
important
topic
in
organic
synthesis
pharmacochemistry.
Herein,
a
novel
Pd/Mengphos
complex
was
designed
applied
palladium-catalyzed
high-order
[4+4]
cycloaddition
2-substituted
allylic
carbonates
to
α,β-unsaturated
imines,
allowing
facile
access
versatile
good
yields
with
excellent
b/l
Z/E
selectivities
(up
92%
yield
complete
selectivities).
reaction
exhibited
broad
substrate
scope,
mild
conditions,
functional
group
compatibility.
In
addition,
asymmetric
version
has
also
been
tested,
affording
the
desired
moderate
enantioselectivity.
New Journal of Chemistry,
Год журнала:
2024,
Номер
48(11), С. 4645 - 4669
Опубликована: Янв. 1, 2024
This
review
summarized
the
progress
in
synthesizing
eight-membered
N-heterocycles
over
past
two
decades
(1995–2023),
inspiring
synthetic
chemists
to
develop
more
efficient
strategies
for
construction
of
these
skeletons.
Abstract
Oxazocines
are
key
structural
intermediates
in
the
synthesis
of
natural
products
and
pharmaceutical
molecules.
However,
oxazocines
especially
a
highly
enantioselective
manner,
is
long‐standing
formidable
challenge
due
to
unfavorable
energetics
involved
cyclization.
Herein,
series
new
PNP‐Ligand
P
‐chiral
stereocenter
first
designed
synthesized,
called
MQ‐Phos
,
successfully
applied
it
Pd‐catalyzed
higher‐order
formal
[4+4]‐cycloaddition
α
β
‐unsaturated
imines
with
2‐(hydroxymethyl)‐1‐arylallyl
carbonates.
The
reaction
features
mild
conditions,
excellent
regio‐
enantiocontrol
broad
substrate
scope
(54
examples).
Various
medium‐sized
rings
can
be
afforded
moderate
yields
(up
92%)
enantioselectivity
99%
ee).
newly
developed
critical
for
ring
catalytic
reactivity
enantioselectivity.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(21), С. 4521 - 4527
Опубликована: Авг. 7, 2024
Abstract
Catalyst‐controlled
switchable
(4+3)
and
(4+2)
annulation
reactions
of
Morita–Baylis–Hillman
carbonates
with
benzofuran‐derived
azadienes
have
been
established.
Employing
PCy
3
as
the
catalyst,
reaction
could
provide
a
variety
synthetically
useful
benzofuro[3,2‐
b
]azepines
in
good
yields
(80–92%)
excellent
chemo‐
regioselectivities
via
cycloaddition
reactions.
Whereas
changing
catalyst
from
to
DMAP,
were
switched
construct
highly
substituted
spirotetrahydroquinoline
scaffolds
three
sequential
stereocenters
containing
all‐carbon
spiro‐quaternary
efficiency
diastereoselectivities
(92–96%
all
cases>25:1
dr
)
annulations.
In
addition,
synthetic
utility
this
method
was
further
showcased
by
gram‐scale
transformations
product.
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.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
11(5), С. 1299 - 1304
Опубликована: Дек. 25, 2023
This
work
introduces
a
novel
α,α-diester-δ-vinylvalerolactone
as
dipolar
precursor
in
palladium-catalyzed
[6
+
4]
cycloaddition
reaction
with
azadienes,
resulting
the
production
of
ten-membered
heterocycles.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
22(2), С. 252 - 268
Опубликована: Ноя. 28, 2023
Eight-membered
heterocycles
are
important
but
their
synthesis
is
usually
challenging.
This
review
summarizes
the
recent
advances
in
[4
+
4]
annulation
of
conjugated
heterodienes
with
1,4-dipolar
species
for
assembling
eight-membered
heterocycles.
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.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 16, 2024
Comprehensive
Summary
We
report
a
palladium‐catalyzed
asymmetric
[4+4]
cycloaddition
reaction
between
2‐alkylidenetrimethylene
carbonate
and
electron‐deficient
indole‐2,3‐quinodimethanes
(
IQDMs
).
This
features
exclusive
regioselectivity,
high
yield
(up
to
98%),
excellent
enantioselectivity
95%
ee),
easy
scale‐up
without
any
loss
of
efficiency,
making
it
valuable
for
the
synthesis
indole‐fused
eight‐membered
oxa‐rings.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
11(3), С. 696 - 702
Опубликована: Ноя. 30, 2023
A
Pd-catalyzed
chemodivergent
cyclization
strategy
of
TMM
with
formyl
cinnamates
by
regulating
solvents
and
cocatalysts
is
proposed,
affording
hexahydrocyclopenta[
a
]inden-8-ols,
tetrahydro-2
H
-indeno[1,2-
b
]furans
aryl
cyclopentenes
in
good
yields.
