Stereoselective Synthesis of Functionally Rich Spirooctahydroquinoline Oxindoles via Enynamide Cycloisomerisation/[4+2]‐Addition Sequence
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(9), С. 2014 - 2019
Опубликована: Март 18, 2024
Abstract
Creating
an
expedient
method
for
synthesizing
biologically
significant
functionally
rich
octahydroquinoline
is
a
highly
sought‐after
yet
challenging
endeavour.
In
this
report,
we
document
unprecedented
approach
to
the
construction
of
novel
spirooctahydroquinoline
oxindole
architectures.
The
reaction
proceeds
through
Pd
(II)
catalyzed
cycloisomerisation
and
quinine
[4+2]‐addition
sequence
afford
desired
adduct
in
moderate
excellent
yield
(up
89%)
single
diastereomer
with
three
contiguous
stereocenters
including
one
spirocenter.
An
overwhelming
number
libraries
were
generated
(35
examples)
reflecting
synthetic
versatility
functional
groups/substituents
tolerance.
Further,
transformed
into
medicinally
important
fluoro‐decahydroepoxyethanoquinoline
spirooxindole
scaffold
five
selectivity
(95%
>99:1
dr)
steps
which
signifies
utility
developed
methodology.
Язык: Английский
TMSCl-Promoted Sulfonylation of Propargylic Alcohols with Sodium Sulfinates for the Construction of (E)-1,3-Disulfonylpropenes and (E)-1-Sulfonylpropenols
Shimin Jiang,
Meng Liang,
Xi Chen
и другие.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(21), С. 15694 - 15707
Опубликована: Окт. 12, 2024
A
direct
and
novel
transformation
of
propargylic
alcohols
with
sodium
sulfinates
for
the
regio-
stereoselective
synthesis
(
Язык: Английский
Lewis Acid‐Catalyzed Tandem Annulation of Propargylic Alcohols with 2‐Allylphenols and Their Anti‐tumor Activities
Xiang Li,
Ning-Yu Guo,
Qing-Hui Liu
и другие.
Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Авг. 19, 2024
Abstract
A
novel
bismuth(III)
trifluoro‐methanesulfonate‐catalyzed
and
environmentally
benign
synthetic
strategy
for
the
construction
of
a
wide
range
structurally
diverse,
sophisticated
[5,6,5]‐oxygen‐containing
tricyclic
frameworks
with
easy‐to
handle
propargylic
alcohols
2‐allylphenols
as
substrates
in
presence
Bi(OTf)
3
AgOTf
is
described.
This
Lewis
acid
catalyzed
[3+2]
annulation
protocol,
which
tolerates
great
deal
functional
groups,
proceeds
through
sequential
Meyer‐Schuster
rearrangement,
nucleophilic
substitution,
5‐
exo
‐trig
cyclization,
endo
proton
exchange
sequences,
affording
versatile
approach
accessing
oxygen‐containing
skeletons
moderate‐to‐excellent
yields.
In
addition,
most
obtained
compounds
exhibited
anti‐tumor
activities
against
three
types
human
cancer
cell
lines
vitro
,
including
Caco‐2
colon
cells,
MCF‐7
breast
Hepg‐2
liver
cells.
Язык: Английский