Abstract
We
describe
herein
the
additive‐controlled
divergent
[4+2]
cycloaddition
and
1,4‐Michael
addition
reaction
of
benzofuran‐derived
azadienes
(BDAs)
with
enamides.
An
unprecedented
BDAs
enamide
compounds
was
developed
in
presence
4
Å
MS,
providing
a
variety
structurally
complex
decahydrobenzofuro[3,2‐
b
]quinolines
(13
examples)
moderate
to
excellent
yields
(59–98
%
yields)
single
diastereoisomer
obtained.
While
employing
MgSO
as
desiccant,
chemoselectivity
switched
1,4‐addition
reactions,
leading
wide
range
highly
functionalized
hybrids
benzofurans
(25
25–94
under
mild
conditions.
Chemical Society Reviews,
Год журнала:
2022,
Номер
51(10), С. 4146 - 4174
Опубликована: Янв. 1, 2022
The
advances
on
metal-catalysed
high-order
dipolar
annulations
were
comprehensively
summarized
in
this
review.
To
further
exploit
the
potential
of
unique
annulation
strategy,
a
research
outlook
was
also
proposed.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
63(6)
Опубликована: Дек. 15, 2023
Abstract
We
report
herein
an
unprecedented
enantioselective
(4+4)
cycloaddition
of
simple
1,3‐dienes
with
azadienes
for
the
construction
fused
eight‐membered
N
‐heterocycles.
In
this
transformation,
π‐Lewis
basic
Pd(0)
catalyst
achieves
activation
to
induce
nucleophilic
addition
followed
by
ring
cyclization
via
a
selective
terminal
allylic
substitution.
Furthermore,
highly
efficient
and
diastereoselective
derivatizations
rings
provide
facile
access
diverse
enantiopure
tetra‐
hexacyclic
compounds
potential
application
in
medicinal
chemistry.
ACS Catalysis,
Год журнала:
2024,
Номер
14(20), С. 15743 - 15750
Опубликована: Окт. 9, 2024
Medium-sized
rings
are
important
structural
units
in
organic
molecules
of
significant
interest.
However,
their
efficient
synthesis,
especially
a
highly
enantioselective
manner,
has
been
formidable
challenge.
Herein,
we
report
an
synthesis
medium-sized
aza-rings
by
Z-retentive
asymmetric
allylic
substitution-enabled
intermolecular
cascade
cyclization
via
iridium/cinchona
dual
catalysis.
The
reaction
was
performed
under
mild
conditions
and
with
good
functional
group
tolerance.
Various
nine-
to
eleven-membered
can
be
afforded
moderate
high
yields
(up
98%)
enantioselectivities
93%
ee).
utilization
both
Z-linear
dipole
precursor
binary
catalyst
is
critical
for
the
desired
reactivity.
Organic Chemistry Frontiers,
Год журнала:
2021,
Номер
8(24), С. 7004 - 7008
Опубликована: Янв. 1, 2021
An
efficient
approach
for
the
synthesis
of
azonanes
via
Pd-catalyzed
decarboxylative
[5
+
4]
cycloaddition
has
been
developed.
The
reactions
feature
wide
functional
group
tolerance
with
exclusive
regioselectivity.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(5), С. 3389 - 3401
Опубликована: Фев. 14, 2022
By
virtue
of
a
fundamentally
new
reaction
model
benzofuran-derived
azadienes
(BDAs),
an
unprecedented
synthesis
biologically
important
pyrazoles
has
been
achieved
through
tandem
[3
+
2]
cycloaddition/ring-opening
rearrangement
BDAs
with
nitrile
imines.
The
nature
and
type
substrates
are
found
to
act
as
chemical
switch
trigger
two
distinct
pathways.
A
minor
modification
the
allows
access
spiro-pyrazolines.
Organic Letters,
Год журнала:
2022,
Номер
24(20), С. 3747 - 3752
Опубликована: Май 13, 2022
A
phosphine-catalyzed
(4
+
2)
annulation
of
tetrahydrobenzofuranone-derived
allenoates
and
benzofuran-derived
azadienes
(BDAs)
has
been
achieved
to
construct
the
decahydro-2H-naphtho[1,8-bc]furan
derivatives,
which
were
subsequently
treated
with
4-methylbenzenethiol
trimethylamine
produce
thio-Michael
addition
products
in
high
excellent
yields
good
diastereoselectivities.
Chemical Science,
Год журнала:
2023,
Номер
14(18), С. 4893 - 4900
Опубликована: Янв. 1, 2023
An
enantio-
and
diastereoselective
Pd-catalysed
(3
+
2)
cycloaddition
of
bis(trifluoroethyl)
2-vinyl-cyclopropane-1,1-dicarboxylate
(VCP)
with
cyclic
sulfamidate
imine-derived
1-azadienes
(SDAs)
has
been
developed.
These
reactions
provide
highly
functionalized
spiroheterocycles
having
three
contiguous
stereocentres,
including
a
tetrasubstituted
carbon
bearing
an
oxygen
functionality.
The
two
geminal
trifluoroethyl
ester
moieties
can
be
manipulated
in
facially
selective
manner
to
afford
more
diversely
decorated
spirocycles
four
stereocentres.
In
addition,
reduction
the
imine
moiety
also
fourth
stereocentre
exposes
important
1,2-amino
alcohol
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.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(8), С. 2326 - 2331
Опубликована: Янв. 1, 2024
An
efficient
approach
for
the
construction
of
non-fused
azepines
in
good
yields
with
high
enantioselectivity
via
Pd-catalyzed
asymmetric
[4
+
3]
cycloaddition
was
developed.
