Angewandte Chemie,
Год журнала:
2019,
Номер
132(21), С. 8080 - 8090
Опубликована: Дек. 2, 2019
Abstract
Direct
deprotonation
represents
an
extremely
simple,
straightforward,
and
atom‐economic
strategy
to
activate
pronucleophiles
bearing
acidic
proton.
However,
the
difficulty
often
arises
in
activating
with
high
p
K
a
values
by
using
conventional
chiral
tertiary
amines.
To
overcome
this
challenge,
handful
of
novel
Brønsted
superbases,
including
amidines,
guanidines,
cyclopropenimines,
iminophosphoranes,
have
been
discovered
recent
years.
This
minireview
focuses
on
application
these
organo‐superbases
catalytic
asymmetric
reactions
weakly
pronucleophiles,
highlights
their
comparison
amines,
demonstrating
highly
efficient
processes
stereoselectivity
controlled
conversions
superbases.
The
advantage
new
superbases
brings
great
opportunity
for
developing
more
transformations
pronucleophiles.
The
synthesis
of
chiral
azaarenes
is
great
importance
for
pharmaceutical
development.
A
direct
and
versatile
approach
to
obtaining
such
compounds
the
functionalization
imine-containing
2-vinylazaarenes.
We
have
developed
a
N,N'-dioxide/Mg(II)
Lewis
acid
catalytic
system
control
nucleophilic
β-cyclic
or
acyclic
ketone
amides/esters
overcome
strong
background
reaction,
enabling
highly
efficient
enantioselective
hydroalkylation
2-vinylazaarenes
via
conjugate
addition.
As
result,
library
bearing
an
all-carbon
quaternary
stereocenter
can
be
obtained
in
high
yields
with
good
excellent
ee
values.
DFT
calculations
indicate
assistances
hydrogen
transfer,
CH-π
interaction
between
substrate
ligand's
amide
group
differentiation.
Chemical Communications,
Год журнала:
2020,
Номер
56(11), С. 1693 - 1696
Опубликована: Янв. 1, 2020
Asymmetric
conjugate
addition
of
PhMe2SiBPin
to
a
wide
range
N-heteroaryl
alkenes
proceeded
in
the
presence
copper
catalyst
coordinated
with
chiral
phosphoramidite
ligand
afford
useful
β-silyl
N-heteroarenes
high
yields
and
ees.
Organic Letters,
Год журнала:
2022,
Номер
24(22), С. 3965 - 3969
Опубликована: Май 31, 2022
The
first
catalytic
enantioselective
[3
+
2]
cycloaddition
reaction
between
vinylcyclopropanes
and
alkenyl
N-heteroarenes
in
the
presence
of
LiBr
a
Pd(0)/SEGPHOS
complex
was
developed.
plays
key
role
improving
reactivity
as
mild
Lewis
acid.
Angewandte Chemie,
Год журнала:
2019,
Номер
132(21), С. 8080 - 8090
Опубликована: Дек. 2, 2019
Abstract
Direct
deprotonation
represents
an
extremely
simple,
straightforward,
and
atom‐economic
strategy
to
activate
pronucleophiles
bearing
acidic
proton.
However,
the
difficulty
often
arises
in
activating
with
high
p
K
a
values
by
using
conventional
chiral
tertiary
amines.
To
overcome
this
challenge,
handful
of
novel
Brønsted
superbases,
including
amidines,
guanidines,
cyclopropenimines,
iminophosphoranes,
have
been
discovered
recent
years.
This
minireview
focuses
on
application
these
organo‐superbases
catalytic
asymmetric
reactions
weakly
pronucleophiles,
highlights
their
comparison
amines,
demonstrating
highly
efficient
processes
stereoselectivity
controlled
conversions
superbases.
The
advantage
new
superbases
brings
great
opportunity
for
developing
more
transformations
pronucleophiles.
