Thermodynamic Controlled Regioselective C1-Functionalization of Indolizines with 3-Hydroxyisoindolinones via Brønsted Acid Catalyzed aza-Friedel–Crafts Reaction
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(4), С. 2794 - 2799
Опубликована: Янв. 31, 2024
A
Brønsted
acid
catalyzed
aza-Friedel–Crafts
reaction
of
indolizines
with
3-hydroxyisoindolinones
has
been
established,
which
constructs
isoindolinone
derivatives
bearing
a
tetrasubstituted
stereocenter
in
good
to
high
yields
and
enantioselectivities.
Notably,
this
strategy
provides
new
access
C1-functionalization
excellent
regioselectivities.
Moreover,
intriguing
C1-regioselective
transformation
was
induced
under
thermodynamic
control.
Язык: Английский
Organocatalytic enantio- and diastereoselective synthesis of trifluoro-ethylamine allenoate derivatives containing axial and central chiralities
Chemical Communications,
Год журнала:
2024,
Номер
60(79), С. 11116 - 11119
Опубликована: Янв. 1, 2024
Herein,
we
report
an
example
of
a
stereoselective
γ-addition
reaction
trifluoromethyl
ketimines
to
1-alkynyl
ketones
mediated
by
isothiourea,
BTM,
under
mild
conditions,
which
afforded
tetrasubstituted
allenes
with
central
chiralities
in
high
yields
(up
94%
yield),
good
enantioselectivities
91%
ee),
and
excellent
diastereoselectivities
(all
>20
:
1
dr).
In
addition,
the
BTM-catalyzed
was
successfully
applied
gram-scale
reaction,
unexpected
benzopyrrolothiazine
derivative
converted,
albeit
racemic.
Язык: Английский
Cascade Synthesis of Pyrrolo[1,2-a]quinolines and Pyrrolo[2,1-a]isoquinolines via Formal [3 + 2]-Cycloaddition of Push–Pull Nitro Heterocycles with Carbonyl-Stabilized Quinolinium/Isoquinolinium Ylides
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(14), С. 9816 - 9829
Опубликована: Июнь 25, 2024
Various
substituted
pyrrolo[1,2-
Язык: Английский
Stereoselective Synthesis of Axially Chiral Allenes and Styrenes via Chiral Phosphoric Acid Catalysis: An Overview
ACS Omega,
Год журнала:
2024,
Номер
9(31), С. 33351 - 33364
Опубликована: Июль 26, 2024
Chiral
allenes
and
styrenes
are
essential
components
in
fields
like
medicinal
chemistry,
materials
science,
organic
synthesis.
They
serve
a
crucial
role
as
chiral
ligands
catalysts
asymmetric
Over
the
past
decade,
there
has
been
significant
advancement
development
of
practical
methods
utilizing
organocatalytic
strategies
for
synthesis
styrenes.
It
is
noteworthy
that
despite
extensive
studies
on
formation
styrenes,
existing
reviews
their
construction
confined
to
specific
organocatalysis,
called
phosphoric
acid
catalysis,
less
documented.
This
review
aims
explore
different
conceptual
approaches
based
electrophilic
species
involved
reaction
produce
stereoselective
providing
insights
into
recent
advancements
field.
Emphasis
placed
works
published
since
2017,
with
detailed
discussions
mechanisms
examples
from
literature.
Язык: Английский
Regioselective [3 + 2] Annulation of β,γ-Alkynyl-α-ketimino Esters with 1,3-Dicarbonyls: The Synthesis of Highly Functionalized Dihydrofurans
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 30, 2025
A
regioselective
[3
+
2]
annulation
of
β,γ-alkynyl-α-ketimino
esters
with
1,3-dicarbonyls
is
disclosed.
series
Z-selective
dihydrofurans
bearing
an
exocyclic
double
bond
and
a
quaternary
carbon
center
are
accessed
without
the
usage
base.
Control
deuterium-labeling
experiments
have
been
investigated
to
probe
into
reaction
mechanism.
The
catalyst
base-free
nucleophilic
addition
highlights
transformation.
Язык: Английский
Emerging progress in chiral phosphoric acid-catalyzed asymmetric synthesis of unnatural α-amino acids
Catalysis Science & Technology,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
Unnatural
α-amino
acids
(α-UAAs)
are
essential
components
in
the
development
of
biologically
active
compounds,
pharmaceuticals,
ligands,
and
catalysts.
Язык: Английский
Asymmetric Cascade Dearomatization–Cyclization Reaction of Tryptamines with β,γ-Alkynyl-α-imino Esters: Access to Hexahydropyrrolo[2,3-b]indole-Containing Tetrasubstituted α-Amino Allenoates
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(14), С. 10148 - 10162
Опубликована: Июль 3, 2024
An
organocatalytic
enantio-
and
diastereoselective
synthesis
of
hexahydropyrrolo[2,3-
Язык: Английский
Chiral Phosphoric Acid-Catalyzed Enantioselective Synthesis of Biphenyl-Bridged ɛ-Sultams via Friedel-Crafts Reactions of Cyclic N-Sulfonylimines with Indolizines
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(17), С. 4829 - 4835
Опубликована: Янв. 1, 2024
An
asymmetric
aza-Friedel–Crafts
arylation
of
biphenyl-bridged
seven-membered
cyclic
N
-sulfonylimines
with
indolizines
via
chiral
phosphoric
acid
is
realized,
affording
indolizine
modified
ε-sultams
up
to
99%
yield
and
ee.
Язык: Английский
Enantioselective Assembly of Fully Substituted α‐Amino Allenoates Through a Mannich Addition and Stepwise [3,3]‐σ Rearrangement Sequence
Haoxuan Yuan,
Yi Zhou,
Xiongda Xie
и другие.
Advanced Science,
Год журнала:
2024,
Номер
12(2)
Опубликована: Ноя. 20, 2024
Abstract
Chiral
fully‐substituted
allenes
are
synthetically
significant
and
pivotal
building
blocks
that
can
engage
in
diverse
transformations
toward
a
variety
of
bioactive
molecules.
The
enantioselective
assembly
these
skeletons
using
readily
available
reactants
offers
advantages
but
remains
challenging.
Herein,
an
asymmetric
formal
Michael‐type
addition
alkynyl
imines
with
the
key
alkylgold
intermediates
derived
situ
from
N
‐propargylamides
is
accomplished
under
gold‐complex
chiral
quinine‐derived
squaramide
(QN‐SQA)
synergetic
catalysis.
Control
experiments
density
functional
theory
(DFT)
calculations
indicated
this
cascade
reaction
involves
Mannich‐type
stepwise
[3,3]‐σ
rearrangement
sequence,
leading
to
fully
substituted
α‐amino
allenoates,
which
elusive
take
multi‐step
prepare
other
methods,
high
yields
excellent
enantioselectivity.
Язык: Английский