Rhodium-Catalyzed Asymmetric Hydroselenation of 1-Alkynylindoles for Atroposelective Synthesis of Vinyl Selenoethers
ACS Catalysis,
Год журнала:
2024,
Номер
14(17), С. 13055 - 13064
Опубликована: Авг. 15, 2024
Catalytic
asymmetric
hydrofunctionalization
of
π-bonds
has
been
extensively
studied,
but
the
alkynes
that
affords
atropoisometric
products
remains
heavily
underexplored.
We
herein
report
[Rh(COD)OAc]2/Mg(NTf2)2-catayzed
highly
atroposelective
hydroselenation
two
classes
1-alkynylindoles
using
selenophenols,
where
Mg(II)
salt
both
activates
Rh
catalyst
and
provides
a
key
NTf2
anion
essential
for
catalytic
activity
enantioselectivity,
affording
C–N
axially
chiral
trisubstituted
olefins
bear
relatively
low
racemization
barrier
(ΔG‡
∼
27
kcal/mol).
The
system
features
high
activity,
mild
reaction
conditions,
good
functional
group
tolerance,
regio-,
(E)-,
enantioselectivity.
selenoether
moiety
in
product
framework
can
be
readily
functionalized
to
give
synthetically
useful
products.
Язык: Английский
Chiral Lewis Base/Achiral Acid Co‐Catalyzed Atroposelective Sulfenylation of Pyrrole Derivatives: Construction of C—N Axially Chiral Sulfides
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(17), С. 2005 - 2009
Опубликована: Апрель 25, 2024
Comprehensive
Summary
Chiral
BINAM‐derived
selenide/achiral
acid
co‐catalyzed
atroposelective
electrophilic
sulfenylation
of
pyrrole
derivatives
has
been
realized
for
the
first
time.
A
variety
C—N
axially
chiral
sulfur‐containing
were
readily
obtained
in
moderate
to
good
yields
with
excellent
enantioselectivities.
This
catalytic
system
involves
sequential
desymmetrization
and
kinetic
resolution.
Язык: Английский
Recent Advances in Catalytic Transformations of ortho-Alkynylnaphthols
Tetrahedron,
Год журнала:
2025,
Номер
unknown, С. 134726 - 134726
Опубликована: Май 1, 2025
Язык: Английский
Recent Developments in Selenylation of Alkynes
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
unknown
Опубликована: Июль 29, 2024
Abstract
Alkynes
are
simple
yet
important
organic
feedstocks.
The
selenylation
of
alkynes
is
able
to
produce
complex
selenium‐containing
compounds
in
a
facile
way.
Although
there
some
reviews
about
the
alkynes,
most
them
focus
on
one
specific
reaction
or
what
types
products
that
can
be
obtained.
There
lack
attention
given
various
uses
different
selenium
reagents
and
their
mechanisms.
This
review
mainly
focuses
recent
advances
(2013–2023)
based
diverse
reagents.
Mechanisms
how
added
work
will
discussed.
Different
types,
including
difunctionalization,
Se‐annulation,
spiro‐cyclization,
C−Se
coupling,
click
recorded
this
review.
regioselectivity
achieved
through
mechanisms,
radicals,
seleniraniums
electrophilic
cyclization.
We
hope
it
do
help
for
future
research
area.
Язык: Английский
TCCA/RSeSeR-Mediated Selenoalkoxy of Allenamides via a Radical Process: Synthesis of Selanyl-allylic N,O-Aminals
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(21), С. 15529 - 15541
Опубликована: Окт. 18, 2024
An
efficient
TCCA
(trichloroisocyanuric
acid)/RSeSeR-mediated
selenoalkoxy
of
allenamides
for
the
construction
selanyl-allylic
N,OA-aminal
derivatives
was
developed.
The
reaction
exhibits
good
functional
group
tolerance
and
high
efficiency,
affording
products
in
to
excellent
yields.
Mechanistic
investigations
indicated
that
a
radical
intermediate
first
formed
via
RSe
added
central
carbon
allenamides,
which
subsequently
furnished
highly
stable
carbocation
by
abstraction
an
electron
chlorine
radical.
Moreover,
this
is
report
using
selenium
reagent
(RSeCl)
activate
process.
Язык: Английский