Access to Tetrahydrothiopyrano[2,3‐b]Indole Derivatives via Zinc‐Catalyzed Asymmetric [3+3] Annulation of Indoline‐2‐Thiones with Yne–Enones
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(8), С. 1770 - 1775
Опубликована: Март 1, 2024
Abstract
We
report
herein
an
enantioselective
[3+3]
annulation
of
indoline‐2‐thiones
with
yne–enones
by
chiral
dinuclear
zinc
catalysts
via
a
Brønsted
base
and
Lewis
acid
cooperative
activation
model.
This
transformation
proceeded
through
sequential
conjugate
addition,
allenyl
ketone
formation
intramolecular
sulfa‐Michael
6‐
endo
‐trig
cyclization.
A
range
enantioenriched
tetrahydrothiopyrano[2,3‐
b
]indole
derivatives
bearing
exocyclic
double
bond
were
obtained
in
moderate
yields
excellent
stereoselectivities
(up
to
20
:
1
dr,
20:1
Z/E
ratio
95%
ee).
Late‐stage
functionalization,
large‐scale
experiment
further
derivatizations
also
explored.
Язык: Английский
Asymmetric synthesis of bicyclic pyran scaffolds bearing two oxa-quaternary stereocenters via zinc-catalyzed [5 + 1] annulations
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(18), С. 4516 - 4521
Опубликована: Янв. 1, 2023
Zinc-catalyzed
[5
+
1]
annulation
of
α-hydroxyl
aryl
ketones
with
cyclohexadienone-tethered
enones
has
been
developed,
giving
access
to
enantioenriched
bicyclic
pyran
scaffolds
bearing
two
oxa-quaternary
stereocenters.
Язык: Английский
Manipulating Activity and Chemoselectivity of a Benzaldehyde Lyase for Efficient Synthesis of α-Hydroxymethyl Ketones and One-Pot Enantio-Complementary Conversion to 1,2-Diols
ACS Catalysis,
Год журнала:
2024,
Номер
14(13), С. 9687 - 9700
Опубликована: Июнь 13, 2024
The
α-hydroxymethyl
ketone
motif
has
been
widely
found
in
many
pharmaceutically
important
molecules
and
used
as
a
key
intermediate
the
synthesis
of
various
fine
chemicals
natural
products.
Hydroxymethylation
aldehydes
with
formaldehyde
catalyzed
by
thiamine
diphosphate
(ThDP)-dependent
enzymes
is
considered
highly
valuable
approach
terms
atom
economics
sustainability,
while
low
activity
chemoselectivity
restricted
its
widespread
application.
In
this
study,
benzaldehyde
lyase
(BAL)
high
catalytic
efficiency
was
acquired
enzyme
screening
engineering,
which
hydroxymethylation
furfural
at
concentration
700
mM.
Crystal
structural
analysis
molecular
dynamics
studies
revealed
that
BAL
were
improved
reshaping
conformation
substrate
entrance
tunnel.
Furthermore,
one-pot
concurrent
enzymatic
process
involving
BAL-catalyzed
subsequent
asymmetric
reduction
carbonyl
reductase
developed,
offering
efficient
way
to
produce
chiral
1,2-diols
from
simple
aldehydes,
ee
values
(97–99%)
good
yields
(52–97%).
significantly
demonstrated
potential
engineered
industrial
production
ketones,
could
readily
enable
other
high-value-added
formaldehyde.
Язык: Английский
Enantioselective access to spiro[2,3-dihydrofuran-2,2′-inden-1-ones]viazinc catalyzed [3 + 2] annulation of α-hydroxy-1-indanones with yne–enones
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(16), С. 4061 - 4067
Опубликована: Янв. 1, 2023
An
enantioselective
construction
of
spiro[1-indanone-dihydrofurans]
has
been
accomplished
through
zinc-catalyzed
[3
+
2]
annulation
via
a
Brønsted
base
and
Lewis
acid
cooperative
activation
model.
Язык: Английский
Dinuclear Zinc Catalyzed [3+2] Annulation of Benzylideneindolinones Access to CF3‐Containing 2,3‐Pyrrolidinyl Dispirooxindoles
Ying‐Hui Zhai,
Ya‐Jun Guo,
Si‐Si Du
и другие.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(18), С. 3088 - 3093
Опубликована: Авг. 9, 2023
Abstract
This
report
has
realized
the
catalytic
asymmetric
[3+2]
annulation
of
benzylideneindolinones
with
CF
3
‐containing
isatin‐derived
azomethine
ylides
for
first
time,
in
which
organocatalysis
failed.
In
presence
dinuclear
zinc
catalysts,
a
series
functionalized
2,3‐pyrrolidinyl
dispirooxindoles
have
been
synthesized
good
yields
excellent
stereoselectivity
under
mild
reaction
conditions.
protocol
can
be
run
on
gram
scale
and
possible
mechanism
is
proposed.
Язык: Английский
Dinuclear Zinc‐Catalyzed Asymmetric Desymmetrization of Cyclopentendiones: Access to Functional Cyclopentanediones Bearing an All‐carbon Quaternary Stereocenter
Chemistry - An Asian Journal,
Год журнала:
2023,
Номер
18(18)
Опубликована: Авг. 1, 2023
The
success
in
the
identification
of
two
enantioisomeric
surfaces
electrophiles
by
dinuclear
zinc
catalysts
is
disclosed.
This
protocol
realizes
a
zinc-cocatalyzed
desymmetrization
cyclopentendiones
using
α-hydroxy
aryl
ketones
as
nucleophiles
through
Michael
addition
reaction.
Under
mild
conditions,
series
functional
cyclopentanediones
bearing
multiple
stereogenic
centers
including
an
all-carbon
quaternary
stereocenter,
were
obtained
moderate
to
good
yields
with
excellent
stereoselectivities.
Язык: Английский
Dinuclear zinc catalysis of a kinetic resolution strategy for distinguishing one pair of diastereoisomers from multiple stereoisomers
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(18), С. 5172 - 5178
Опубликована: Янв. 1, 2024
A
new
kinetic
resolution
strategy
of
distinguishing
four
stereoisomers
is
realized
by
dinuclear
zinc
catalysts.
Язык: Английский
Heterobimetallic Zinc/Strontium Catalysis: Z/E-Selective Asymmetric Conjugate Addition of 3-Acetoxy-2-oxindoles to Alkynones
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(17), С. 12307 - 12317
Опубликована: Авг. 27, 2024
A
chiral
Zn–Sr
heterobimetallic
catalyst
system
generated
in
situ
has
been
developed
for
the
first
highly
Z/E-selective
asymmetric
conjugate
addition
of
3-acetoxy-2-oxindoles
to
alkynones.
Both
terminal
alkynones
and
nonterminal
could
be
applied
catalytic
system.
The
corresponding
3-alkenyl-3-acyloxy-2-oxindoles
were
obtained
moderate
excellent
yields
(55–99%)
with
high
E:Z
ratios
(8:1–30:1)
enantioselectivities
(86–99%
ee).
Язык: Английский