Enantioselective Synthesis of Indole-Fused Polycycles Bearing Four Consecutive Stereocenters via Rhodium Catalysis
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 3, 2025
Indole-fused
polycycles
are
common
in
natural
products
and
bioactive
molecules,
yet
their
concise
efficient
synthesis
remains
challenging,
especially
for
compounds
with
multiple
stereocenters.
Herein,
we
report
the
application
of
a
chiral
CpxRhIII
catalyst
enantioselective
C–H
activation/[4+2]
annulation
indoles
bicyclic
alkenes.
This
catalytic
system
exhibits
high
enantioselectivity
broad
functional
group
tolerance
operates
under
benign
conditions.
The
scope
this
methodology
encompasses
variety
substrates,
delivering
novel
polycyclic
four
consecutive
stereocenters
bridged
ring
good
to
excellent
yields
remarkable
enantioselectivities
(≤1:99
er).
approach
facilitates
structurally
diverse
molecules
that
retain
integrity
while
introducing
chirality.
More
importantly,
3ab
significantly
inhibited
proliferation
CESS
Kasumin-1
cells
IC50
values
0.76
0.28
μM,
respectively.
In
addition,
has
been
demonstrated
as
an
effective
agent
promoting
apoptosis
cells.
Language: Английский
Theoretical Study on the Mechanism of Ru(II)-Catalyzed Intermolecular [3 + 2] Annulation between o-Toluic Acid and 3,5-Bis(trifluoromethyl)benzaldehyde: Octahedral vs Trigonal Bipyramidal
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 23, 2024
Density
functional
theory
was
utilized
to
investigate
the
mechanism
of
Ru(II)-catalyzed
aromatic
C-H
activation
and
addition
aldehydes.
The
proposed
catalytic
cycle
consists
bond
activation,
aldehyde
carbonyl
insertion
for
C-C
coupling,
lactonization
formation
final
product,
product
separation,
catalyst
recovery.
Our
calculations
suggest
that
Ru(OAc)
Language: Английский
Ortho-allylation of anilines with vinylaziridines in hexafluoroisopropanol
Jingjing Nie,
No information about this author
Zhong‐Xia Wang
No information about this author
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 14, 2024
Reaction
of
N
,
-dialkylanilines
with
2-vinylaziridines
in
hexafluoroisopropanol
affords
2-monoallylated
anilines
(
E
)-configured
C–C
double
bonds.
Language: Английский
Mn(I)‐Catalyzed C–H Allylation of Indoles with 2‐Vinylaziridines
Asian Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Oct. 8, 2024
Abstract
Mn(CO)
5
Br‐catalyzed
reaction
of
1‐(2‐pyrimidyl)indoles
with
1‐sulfonyl‐2‐vinylaziridines
in
THF
the
presence
0.25
equiv.
NaOAc
affords
2‐allylated
indoles
31
%
to
100
yields.
The
protocol
suits
for
3‐,
4‐,
5‐,
6‐,
and
7‐substituted
N‐(2‐pyrimidyl)pyrroles
as
well
various
1‐(arylsulfonyl)‐2‐vinylaziridines
such
1‐(phenylsulfonyl)‐2‐vinylaziridine,
1‐(naphthalen‐2‐ylsulfon‐yl)‐2‐vinylaziridine,
1‐(substituted
phenylsulfonyl)‐2‐vinylazirid‐ines.
Functional
groups
including
alkyl,
alkoxy,
halogen,
CHO,
COOMe,
CF
3
,
CN,
NO
2
are
tolerated.
Language: Английский