Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(35), С. 24663 - 24669
Опубликована: Авг. 20, 2024
Chiral
borane–catalyzed
reactions
have
recently
emerged
as
a
powerful
tool
for
the
enantioselective
production
of
chiral
scaffolds.
In
this
study,
we
demonstrated
first
time
that
bisborane
catalyst
can
be
used
α-functionalization
2-alkylazaarenes;
specifically,
accomplished
unprecedented
highly
α-alkylation
unactivated
2-alkylbenzoxazoles
with
electron-deficient
olefins.
The
strong
Lewis
acidity
and
steric
bulk
were
essential
to
observed
reactivity
selectivity.
Angewandte Chemie International Edition,
Год журнала:
2020,
Номер
59(42), С. 18452 - 18456
Опубликована: Июль 8, 2020
Abstract
Herein,
we
report
that
highly
chemoselective
and
enantioselective
reduction
of
2‐vinyl‐substituted
pyridines
has
been
achieved
for
the
first
time.
The
reaction,
which
uses
chiral
spiro‐bicyclic
bisboranes
as
catalysts
HBpin
an
acidic
amide
reducing
reagents,
proceeds
through
a
cascade
process
involving
1,4‐hydroboration
followed
by
transfer
hydrogenation
dihydropyridine
intermediate.
retained
double
bond
in
products
permits
their
conversion
to
natural
other
useful
heterocyclic
compounds
simple
transformations.
Chinese Journal of Chemistry,
Год журнала:
2020,
Номер
38(6), С. 625 - 634
Опубликована: Фев. 17, 2020
The
chemistry
of
frustrated
Lewis
pairs
(FLPs)
provides
the
most
important
approach
for
metal‐free
hydrogenation
and
hydrosilylations.
Great
progress
has
been
achieved
in
this
area
past
decade.
Some
promising
results
have
also
obtained.
This
perspective
article
mainly
focuses
on
recent
advances
synthesis
chiral
acidic
boranes
category
three
protocols,
1)
hydroboration
internal
alkenes
with
Piers’
borane
HB(C
6
F
5
)
2
;
2)
situ
or
alkynes
without
any
purification;
3)
substitution
reaction
(C
n
BCl
3–
organometallic
reagents,
as
well
their
applications
asymmetric
hydrogenations
image
ACS Omega,
Год журнала:
2021,
Номер
6(15), С. 10415 - 10427
Опубликована: Апрель 7, 2021
An
iridium-catalyzed
transfer
hydrogenation
of
N-heteroarenes
to
access
a
series
substituted
1,2,3,4-tetrahydroquinoline
derivatives
in
excellent
yields
is
disclosed.
This
transformation
distinguished
with
water-soluble
and
air-stable
iridium
complexes
as
the
catalyst,
formic
acid
hydrogen
source,
mild
reaction
conditions,
broad
functional
group
compatibility.
Most
importantly,
tentative
chiral
N,N-chelated
Cp*Ir(III)
complex-catalyzed
enantioselective
also
presented,
affording
products
good
enantioselectivities.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(5), С. 3335 - 3339
Опубликована: Фев. 17, 2023
A
chiral
phosphoric
acid
catalyzed
asymmetric
transfer
hydrogenation
of
quinolines
with
regenerable
dihydrophenanthridine
derived
by
a
borane-catalyzed
phenanthridine
under
H2
has
been
successfully
realized.
Despite
the
competition
racemic
pathway,
variety
tetrahydroquinolines
were
furnished
in
high
yields
up
to
91%
ee.
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(35), С. 24663 - 24669
Опубликована: Авг. 20, 2024
Chiral
borane–catalyzed
reactions
have
recently
emerged
as
a
powerful
tool
for
the
enantioselective
production
of
chiral
scaffolds.
In
this
study,
we
demonstrated
first
time
that
bisborane
catalyst
can
be
used
α-functionalization
2-alkylazaarenes;
specifically,
accomplished
unprecedented
highly
α-alkylation
unactivated
2-alkylbenzoxazoles
with
electron-deficient
olefins.
The
strong
Lewis
acidity
and
steric
bulk
were
essential
to
observed
reactivity
selectivity.
