Angewandte Chemie,
Год журнала:
2024,
Номер
136(21)
Опубликована: Март 21, 2024
Abstract
The
construction
of
two
distal
stereocenters
through
a
single
catalytic
process
is
great
interest
in
organic
synthesis.
While
there
are
some
successful
reports
regarding
stereodivergent
preparation
1,3‐
or
1,4‐stereocenters,
the
more
challenged
1,5‐nonadjacent
have
never
been
achieved
fashion.
Herein
we
describe
synergistic
palladium/copper
catalysis
for
1,4‐difunctionalization
reactions
1,3‐dienes,
providing
access
to
quaternary
stereocenters.
Because
each
catalysts
separately
controlled
one
newly
formed
stereocenters,
synthesis
all
four
diastereomers
products
could
readily
be
simply
by
choosing
an
appropriate
combination
chiral
catalysts.
Experimental
and
computational
studies
supported
mechanism
involving
Heck/Tsuji–Trost
cascade
reaction,
origins
stereoselectivity
were
elucidated.
Angewandte Chemie,
Год журнала:
2024,
Номер
unknown
Опубликована: Апрель 2, 2024
Abstract
Spiroaminals
represent
novel
structural
motifs
prevalent
in
diverse
natural
products
and
biologically
active
molecules.
Achieving
their
enantioselective
synthesis
is
a
highly
desirable
challenging
task
synthetic
endeavors
due
to
intricate
molecular
frameworks.
Herein,
we
accomplished
the
first
stereodivergent
construction
of
spiroaminals
using
chiral
bifunctional
organocatalyzed
intramolecular
1,2‐addition
followed
by
an
oxa‐Michael
addition
cascade
high
atom
step
economical
pathway.
A
proper
modulation
cinchona‐derived
squaramide
catalysts
efficiently
provided
access
all
possible
stereoisomers
with
yield,
diastereoselectivity,
excellent
enantioselectivity
while
displaying
broad
substrate
tolerance.
Additionally,
validated
scalability
reaction
demonstrated
variable
spiroaminal
scaffolds,
confirming
viability
our
protocol.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(13), С. 3692 - 3699
Опубликована: Янв. 1, 2024
An
Ir-catalyzed
enantioselective
cascade
allylation/cyclization
reaction
of
2-(1-hydroxyallyl)phenols
was
developed,
affording
antifungal
2-amino-4
H
-chromene
derivatives
with
good
to
excellent
enantioselectivities.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(18), С. 5196 - 5201
Опубликована: Янв. 1, 2024
A
linear
asymmetric
allylic
alkylation
of
vinyloxirane
catalyzed
by
a
chiral
oxalamide–phosphine
(COAP)/Pd(0)
complex
was
reported.
Various
3,3′-oxindole
derivatives
were
achieved
in
good
yields
with
excellent
regio-
and
enantioselectivity.
JACS Au,
Год журнала:
2023,
Номер
4(1), С. 164 - 176
Опубликована: Дек. 21, 2023
Dpp-imines
are
classic
model
substrates
for
synthetic
method
studies.
Here,
we
disclose
their
powerful
use
as
achiral
coligands
in
metal-catalyzed
reactions.
It
is
highly
interesting
to
find
that
the
Dpp-imine
can
not
only
act
ligand
create
excellent
chiral
pockets
with
magnesium
complexes
but
also,
more
importantly,
this
coligand
dramatically
enhance
catalytic
ability
of
metal
catalyst.
The
underlying
reaction
mechanism
was
extensively
explored
by
conducting
a
series
experiments,
including
Angewandte Chemie,
Год журнала:
2024,
Номер
136(21)
Опубликована: Март 21, 2024
Abstract
The
construction
of
two
distal
stereocenters
through
a
single
catalytic
process
is
great
interest
in
organic
synthesis.
While
there
are
some
successful
reports
regarding
stereodivergent
preparation
1,3‐
or
1,4‐stereocenters,
the
more
challenged
1,5‐nonadjacent
have
never
been
achieved
fashion.
Herein
we
describe
synergistic
palladium/copper
catalysis
for
1,4‐difunctionalization
reactions
1,3‐dienes,
providing
access
to
quaternary
stereocenters.
Because
each
catalysts
separately
controlled
one
newly
formed
stereocenters,
synthesis
all
four
diastereomers
products
could
readily
be
simply
by
choosing
an
appropriate
combination
chiral
catalysts.
Experimental
and
computational
studies
supported
mechanism
involving
Heck/Tsuji–Trost
cascade
reaction,
origins
stereoselectivity
were
elucidated.
