Enantioselective Synthesis of 1-Dihydrobenzazepines through Rh2(II)-Catalyzed Cycloisomerization of 1,6-Enyne
Journal of the American Chemical Society,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 13, 2025
The
1-dihydrobenzazepine
skeleton
has
emerged
as
a
privileged
structural
motif
in
bioactive
molecules.
However,
due
to
lack
of
asymmetric
methodology,
access
chiral
1-dihydrobenzazepines
remained
limited.
Herein,
we
report
the
first
intermolecular
cycloisomerization
benzo-fused
enynes
for
synthesis
via
dirhodium
catalysis.
This
methodology
features
high
efficiency
(up
98%
yield),
enantioselectivity
99%
ee),
and
broad
scope
nucleophiles,
including
oxygen
nucleophiles
(alcohols,
phenols,
carboxylic
acids)
carbon
(silyl
enol
ethers).
Theoretical
experimental
mechanistic
studies
reveal
that
reaction
pathway
encompasses
an
cycloisomerization,
which
gives
rise
carbene
containing
donor–acceptor
(D-A)
cyclopropane
moiety,
followed
by
ring-opening
process
stereoselective
nucleophilic
attack
external
on
cyclopropyl
ring.
Control
experiments
demonstrate
pivotal
role
terminal
group
capped
alkynyl
substrates
achieving
good
efficiency.
Язык: Английский
Regioselective electrochemical radical cascade cyclization of internal alkynes to selenated and trifluoromethylated dihydropyran
Science China Chemistry,
Год журнала:
2023,
Номер
66(11), С. 3178 - 3185
Опубликована: Окт. 7, 2023
Язык: Английский
Visible-Light-Induced Regioselective Cascade Radical Cyclization of α-Bromocarbonyls: Access to Benzazepine Derivatives
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(4), С. 2238 - 2246
Опубликована: Янв. 31, 2024
Visible-light-induced
regioselective
cascade
radical
cyclization
of
α-bromocarbonyls
for
the
synthesis
benzazepine
derivatives
is
described.
In
presence
fac-Ir(ppy)3
(2.0
mol
%)
as
a
photocatalyst,
2,6-lutidine
base,
and
dichloromethane
solvent,
reactions
proceed
smoothly
to
afford
seven-membered
rings
in
good
yields.
This
protocol
features
broad
substrate
scope,
excellent
functional
group
tolerance,
mild
reaction
conditions.
Preliminary
mechanistic
studies
reveal
that
generation
α-carbon
more
prone
react
with
1,1-diphenylethylene
tethered
acrylamide
generate
stable
heterocycle.
Язык: Английский
The literature of heterocyclic chemistry, part XXII, 2022
Advances in heterocyclic chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
Язык: Английский
Brønsted-acid-mediated cyclocondensation towards dihydro-1-benzazepines
Tetrahedron Letters,
Год журнала:
2025,
Номер
162, С. 155572 - 155572
Опубликована: Апрель 10, 2025
Язык: Английский
The radical chemistry of N-sulfenyl phthalimides/succinimides for C S bonds formation
Tetrahedron Letters,
Год журнала:
2024,
Номер
144, С. 155153 - 155153
Опубликована: Июнь 17, 2024
Язык: Английский
Electrochemical Oxidation Decarboxylative Cyclization of α-Keto Acid with o-Aminobenzylamine
Chinese Journal of Organic Chemistry,
Год журнала:
2024,
Номер
44(3), С. 972 - 972
Опубликована: Янв. 1, 2024
Язык: Английский
Diastereoselective Dearomatization of Chalcone‐Based Quinolinium Salts to Assemble Bridged Quinobenzazepine Polycycles
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
unknown
Опубликована: Сен. 13, 2023
Abstract
Quinobenzazepines
are
useful
in
medicinal
chemistry,
but
their
synthesis
is
very
challenging.
Herein,
we
designed
and
synthesized
a
range
of
multi‐functional
chalcone‐based
quinolinium
salts;
synthetic
application
the
rapid
straightforward
construction
quinobenzazepines
was
successfully
explored.
A
wide
oxa‐bridged
quinobenzazepine
polycycles
were
afforded
serendipitously
through
dearomative
cascade
reaction
our
newly
developed
salts
acetylacetone.
This
strategy
features
high
bond‐
ring‐forming
efficiency
complete
regio‐
diastereoselective
control.
Язык: Английский