Recent Progress in Chiral Quaternary Ammonium Salt-Promoted Asymmetric Nucleophilic Additions
ACS Catalysis,
Год журнала:
2025,
Номер
15(3), С. 1973 - 2001
Опубликована: Янв. 20, 2025
Chiral
quaternary
ammonium
ion-pair
organocatalysis
has
been
widely
used
in
the
facile
synthesis
of
chiral
molecules
with
challenging
stereocenters.
Especially,
numerous
asymmetric
nucleophilic
addition
reactions
have
facilitated
this
strategy.
This
review
systematically
summarizes
additions
promoted
by
salts
past
decade.
The
content
is
organized
according
to
types
electrophiles
involved
these
catalytic
transformations.
Our
own
perspectives
on
future
development
within
highly
active
research
field
are
also
provided.
Язык: Английский
Cycloadditions of 5-Vinyloxazolidine-2,4-diones: A Straightfor-ward Access to the (thio)Hydantoin Scaffold
Опубликована: Апрель 26, 2024
A
palladium-catalyzed
(3+2)
cycloaddition
between
5-vinyloxazolidine-2,4-diones
(VOxD)
and
(thio)isocyanates
is
described.
Under
optimized
conditions,
an
array
of
(thio)hydantoins
was
readily
prepared
enantioselective
version
this
transformation
then
studied.
To
illustrate
the
importance
method,
a
concise
synthesis
two
bioactive
compounds,
nirvanol
mephenytoin,
carried
out.
This
work
emphasizes
synthetic
potential
VOxD
as
useful
precursors
zwitterionic
aza-π-
allylpalladium
II
intermediates.
Язык: Английский
New Synthetic Approaches for the Construction of Enantioenriched Molecules Bearing Quaternary Stereocenters
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(21), С. 4294 - 4322
Опубликована: Авг. 17, 2024
Abstract
Optically
active
molecule
architectures
stand
as
an
important
class
of
organic
compounds
and
occupy
a
key
role
in
academic
industrial
communities.
Particularly,
the
molecules
bearing
quaternary
carbon
are
vital
importance
because
its
favorable
conformation
valuable
three‐dimensional
molecules,
which
frequently
play
broad
spectrum
functional
materials,
pharmaceutical
relevant
natural
agrochemicals.
Over
past
few
decades,
large
number
synthetic
strategies
for
enantioselective
construction
with
chiral
centers
have
been
focus
research
initiatives.
In
this
review,
state‐of‐the‐art
toward
synthesis
enantioenriched
stereocenters
summarized,
could
be
segmented
into
four
categories:
1)
Construction
optically
by
addition
to
prochiral
sp
2
carbon;
2)
all‐carbon
via
substitution
at
non‐chiral
tetra‐substituted
3)
kinetic
resolution;
4)
desymmetrization
reactions.
Язык: Английский
Cycloadditions of 5-Vinyloxazolidine-2,4-diones: A Straightforward Access to the (Thio)hydantoin Scaffold
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(17), С. 12370 - 12377
Опубликована: Авг. 24, 2024
A
palladium-catalyzed
(3
+
2)
cycloaddition
between
5-vinyloxazolidine-2,4-diones
(VOxD)
and
(thio)isocyanates
is
described.
Under
optimized
conditions,
an
array
of
(thio)hydantoins
was
readily
prepared,
enantioselective
version
this
transformation
then
studied.
To
illustrate
the
importance
method,
a
concise
synthesis
two
bioactive
compounds,
nirvanol
mephenytoin,
carried
out.
This
work
emphasizes
synthetic
potential
VOxD
as
useful
precursors
zwitterionic
aza-π-allylpalladiumII
intermediates.
Язык: Английский