Angewandte Chemie,
Journal Year:
2021,
Volume and Issue:
133(52), P. 27370 - 27376
Published: Oct. 21, 2021
Abstract
Described
herein
is
a
novel
Brønsted
acid
catalyzed
intramolecular
hydroalkoxylation/Claisen
rearrangement,
allowing
the
practical
and
atom‐economic
synthesis
of
range
valuable
spirolactams
from
readily
available
ynamides
in
generally
good
to
excellent
yields
with
diastereoselectivities
broad
substrate
scope.
Importantly,
an
unexpected
dearomatization
nonactivated
arenes
heteroaromatic
compounds
involved
this
tandem
sequence.
Moreover,
asymmetric
version
cyclization
was
also
achieved
by
efficient
kinetic
resolution
chiral
phosphoric
catalysis.
In
addition,
[3,3]‐rearrangement
shown
be
kinetically
preferred
over
related
[1,3]‐rearrangement
theoretical
calculations.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(13), P. 9077 - 9086
Published: June 23, 2023
Efficient
synthesis
of
3-aminoquinolines
has
been
demonstrated
from
readily
accessible
N-sulfonyl-1,2,3-triazoles
and
o-acylaniline
derivatives.
This
transformation
involves
the
generation
C-C
C-N
bonds
through
insertion
rhodium
azavinyl
carbenoid
into
a
N-H
bond
followed
by
cyclization
aromatization.
The
important
features
include
good
functional
group
tolerance,
indoloquinoline,
isolation
N-H-inserted
product,
potential
intermediate.
ACS Catalysis,
Journal Year:
2023,
Volume and Issue:
13(13), P. 8803 - 8812
Published: June 19, 2023
Herein,
an
organocatalytic
enantioselective
desymmetrizing
hydroalkoxylation
of
1,4-
and
1,8-diynes
is
disclosed,
which
represents
a
unique
chiral
Brønsted
acid-catalyzed
desymmetrization
diynes.
This
protocol
provides
facile
practical
access
to
enantioenriched
1,3-diaminopropanol
derivatives
γ-butyrolactones
with
wide
substrate
scope
generally
high
enantioselectivities.
Besides,
the
backbones
these
products
constitute
structural
core
numerous
bioactive
molecules,
they
can
serve
as
valuable
precursors
for
expeditious
assembly
versatile
N-
O-heterocycles.
Moreover,
control
experiments
theoretical
calculations
are
employed
confirm
mechanistic
rationale
elucidate
origin
enantioinduction.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(14), P. 3709 - 3717
Published: Jan. 1, 2022
An
efficient
Brønsted
acid
(BA)
catalyzed
intramolecular
dearomatization
cyclization
of
naphthol-ynamides
has
been
developed,
enabling
the
practical
and
divergent
synthesis
two
azaspirocycles
in
high
yields.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(10), P. 2773 - 2778
Published: Jan. 1, 2022
A
new
copper-catalyzed
B–H
bond
insertion
into
α-imino
copper
carbenes
generated
from
azide–ynamide
cyclization
has
been
developed,
leading
to
a
facile
and
practical
synthesis
of
series
α-boryl
amidines.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(23), P. 16315 - 16329
Published: Nov. 15, 2023
Seven-membered
nitrogen
heterocycles
have
a
strong
influence
in
drug
discovery
due
to
their
inherent
3D
character,
which
allows
the
ability
explore
vast
conformational
space
with
biological
target.
Notably,
privileged
1,4-benzodiazepine
scaffold
is
dominant
treating
central
nervous
system
its
binding
affinity
GABAA
receptor.
Herein,
we
report
protocol
for
transformation
of
azidoquinones
p-quinone
fused
5-substituted-1,4-benzodiazepines
(p-QBZDs)
from
InCl3-catalyzed
intermolecular
tandem
cycloannulation
amines
and
aldehydes.
Detailed
mechanistic
studies
reveal
that
EDA
complex
between
InCl3
crucial
determining
reaction
pathway.
In
absence
formation,
proceeds
via
intermediacy
2,3-bridged-2H-azirine
followed
by
regiospecific
addition
an
amine
C═N/ring
opening/cyclization
deliver
p-QBZD
1,2-azide-nitrogen
migration.
case
through
regioselective
aza-Michael
addition/nitrene
insertion
aldehyde
subsequent
cyclization
imidazole
as
secondary
product
without
This
provides
straightforward
access
redox-active
quinone
embedded
diverse
substrate
scopes
would
find
potential
applications
medicinal
chemistry
discovery.
Angewandte Chemie,
Journal Year:
2022,
Volume and Issue:
134(28)
Published: April 27, 2022
Abstract
Medium‐sized
N
,
S
‐heterocycles
have
received
tremendous
interest
due
to
their
biological
activities
and
potential
medical
applications.
However,
asymmetric
synthesis
of
these
compounds
are
extremely
rare.
Described
herein
is
a
catalyst‐dependent
[3,3]‐sigmatropic
rearrangement
sulfoxide‐ynamides,
enabling
divergent
atom‐economic
series
valuable
medium‐sized
in
moderate
good
yields
with
broad
substrate
scope.
Importantly,
excellent
enantioselectivities
been
achieved
via
an
unprecedented
chirality‐transfer.
Moreover,
theoretical
calculations
employed
elucidate
the
origins
stereospecific
[3,3]‐rearrangement.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
10(1), P. 203 - 208
Published: Nov. 24, 2022
An
efficient
copper-catalyzed
formal
[4
+
1]
annulation
of
N
-propargyl
ynamides
with
diketones
has
been
developed,
allowing
practical
and
atom-economic
synthesis
valuable
pyrrole-substituted
dioxoles
in
generally
moderate
to
excellent
yields.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(9), P. 2557 - 2562
Published: Jan. 1, 2022
An
efficient
gold-catalyzed
cascade
cyclization
of
alkenyl
diynes
involving
alkyne
oxidation,
carbene-alkyne
metathesis
and
cyclopropanation
has
been
developed,
affording
various
tetracyclic
γ-lactams
in
moderate
to
good
yields.
