Heteroannulation of Arynes with α-Bromodifluorohydroxamates: An Efficient and General Approach to Access 2,2-Difluoro Indoxyls
Organic Letters,
Год журнала:
2024,
Номер
26(27), С. 5682 - 5688
Опубликована: Июнь 27, 2024
Herein,
we
report
the
first
general
approach
to
access
Язык: Английский
Recent Developments for the Catalytic Asymmetric Synthesis of Indolin-3-one Derivatives
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
2,2-Disubstituted
indolin-3-ones,
which
are
essential
components
in
many
manufactured
chemicals,
dyes,
and
naturally
occurring
bioactive
alkaloids,
have
emerged
as
exciting
synthetic
targets.
Much
attention
has
been
paid
to
accessing
these
units,
particularly
an
asymmetric
fashion,
during
the
last
decade.
In
this
review
article,
we
discuss
current
state
of
available
methods
with
existing
mechanistic
pathways
for
chiral
indolin-3-one
derivatives
under
various
catalytic
systems.
This
overall
presentation
protocols
access
2,2-disubstituted
or
fused
indolin-3-ones
aza-quaternary
centre
is
categorized
based
on
reaction
modes
2-substituted-3H-indole-3-one
other
similar
protocols.
Язык: Английский
Unusual Regio‐ and Chemoselectivity in Oxidation of Pyrroles and Indoles Enabled by a Thianthrenium Salt Intermediate
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
unknown
Опубликована: Июнь 3, 2024
A
dearomative
oxidation
of
pyrroles
to
Δ
Язык: Английский
Total Synthesis of the Proposed Structure of Indolyl 1,2-Propanediol Alkaloid, 1-(1H-Indol-3-yloxy)propan-2-ol
Chemistry,
Год журнала:
2023,
Номер
5(4), С. 2772 - 2784
Опубликована: Дек. 12, 2023
The
first
total
synthesis
of
the
proposed
structure
unprecedented
indolyl
derivative
bearing
1,2-propanediol
moiety
is
described.
Isomerization
3-alkoxyindolines
through
indolenium
intermediates
was
key
step
in
synthesis.
1H,
13C-NMR,
IR,
and
HRMS
spectra
synthetic
compound
drastically
differed
to
those
originally
reported
structure,
which
suggests
natural
product
requires
revision.
Язык: Английский
Unusual Regio‐ and Chemoselectivity in Oxidation of Pyrroles and Indoles Enabled by a Thianthrenium Salt Intermediate
Angewandte Chemie,
Год журнала:
2024,
Номер
unknown
Опубликована: Июнь 3, 2024
Abstract
A
dearomative
oxidation
of
pyrroles
to
Δ
3
‐pyrrol‐2‐ones
is
described,
which
employs
a
sulfoxide
as
oxidant,
in
conjunction
with
carboxylic
acid
anhydride
and
Brønsted
additive.
3‐substituted
undergo
regioselective
give
the
product
isomer
oxygen
has
been
introduced
at
more
hindered
position.
Regioselectivity
rationalized
by
proposed
mechanism
that
proceeds
initial
thianthrenium
introduction
less‐hindered
pyrrole
α‐position,
followed
distal
attack
an
nucleophile
subsequent
elimination
thianthrene.
The
same
reaction
conditions
are
also
able
effect
chemoselective
indoles
indolin‐3‐ones
additionally
2‐hydroxyindolin‐3‐ones.
Here
again,
regio‐
chemoselectivities
through
intermediacy
salt.
Язык: Английский