Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(20), P. 4394 - 4399
Published: May 14, 2024
A
carbene-catalyzed
enantioselective
addition
of
sulfinate
to
ketones
between
2-benzoylbenzaldehyde
and
sulfonyl
chloride
is
disclosed.
Up
now,
the
carbon
heteroatom
nucleophiles
have
effectively
undergone
catalytic
carbonyl
molecules
introduce
functionalities
chirality.
Sulfone,
as
an
important
class
sulfur-containing
functional
groups,
represents
highly
valuable
motifs
in
medicines
natural
products.
It
remains
undeveloped
for
asymmetric
carbonyls.
Herein
we
disclosed
first
synthesis
sulfones
via
N-heterocyclic
carbene
(NHC)
catalysis.
The
behaves
both
oxidant
a
nucleophilic
substrate
this
process.
Experimental
studies
suggested
that
Breslow
intermediate
can
be
SET
oxidized
by
generate
radical.
This
novel
synthetic
approach
carbonyls
also
used
modify
commercially
available
molecules.
Nature Communications,
Journal Year:
2023,
Volume and Issue:
14(1)
Published: Aug. 12, 2023
A
carbene-catalyzed
asymmetric
access
to
chiral
β-cyano
carboxylic
esters
is
disclosed.
The
reaction
proceeds
between
β,β-disubstituted
enals
and
aromatic
thiols
involving
enantioselective
protonation
of
enal
β-carbon.
Two
main
factors
contribute
the
success
this
reaction.
One
involves
in
situ
ultrafast
addition
thiol
substrates
carbon-carbon
double
bond
substrate.
This
converts
almost
all
substrate
a
Thiol-click
Intermediate,
significantly
reducing
concentration
suppressing
homo-coupling
enals.
Another
factor
an
release
from
Intermediate
for
desired
proceed
effectively.
optically
enriched
our
method
can
be
readily
transformed
medicines
that
include
γ-aminobutyric
acids
derivatives
such
as
Rolipram.
In
synthetic
utilities,
control
outcomes
via
modulation
likely
inspire
future
development.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(16), P. 3975 - 3981
Published: Jan. 1, 2023
An
unprecedented
catalytic
sulfonylation
strategy
has
been
developed
through
the
redox
transformation
of
β-sulfinyl
esters,
providing
a
facile
access
to
axially
chiral
sulfone-containing
styrenes
with
VQMs
in
excellent
enantioselectivities.
Catalysts,
Journal Year:
2024,
Volume and Issue:
14(4), P. 219 - 219
Published: March 22, 2024
In
the
past
few
decades,
N-heterocyclic
carbenes
(NHCs)
have
opened
new
field
of
organocatalysis
in
synthetic
organic
chemistry.
This
review
highlights
dramatic
progress
NHC-catalyzed
C–O
bond
formation
based
on
activation
aldehyde
C(sp2)–H
bonds.
The
oxidative
and
redox
transformations
for
synthesis
various
molecules
with
structural
diversity
complexity
are
summarized.
Furthermore,
methods
strategies
NHC
catalysis
emerging
continuously;
thus,
cooperative
Brønsted
acid,
hydrogen-bonding
catalyst,
transition-metal
photocatalyst
also
described.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(20), P. 4394 - 4399
Published: May 14, 2024
A
carbene-catalyzed
enantioselective
addition
of
sulfinate
to
ketones
between
2-benzoylbenzaldehyde
and
sulfonyl
chloride
is
disclosed.
Up
now,
the
carbon
heteroatom
nucleophiles
have
effectively
undergone
catalytic
carbonyl
molecules
introduce
functionalities
chirality.
Sulfone,
as
an
important
class
sulfur-containing
functional
groups,
represents
highly
valuable
motifs
in
medicines
natural
products.
It
remains
undeveloped
for
asymmetric
carbonyls.
Herein
we
disclosed
first
synthesis
sulfones
via
N-heterocyclic
carbene
(NHC)
catalysis.
The
behaves
both
oxidant
a
nucleophilic
substrate
this
process.
Experimental
studies
suggested
that
Breslow
intermediate
can
be
SET
oxidized
by
generate
radical.
This
novel
synthetic
approach
carbonyls
also
used
modify
commercially
available
molecules.
