Angewandte Chemie,
Journal Year:
2018,
Volume and Issue:
130(21), P. 6407 - 6411
Published: April 12, 2018
Abstract
The
formal
[3+2]
cycloaddition
of
epoxides
and
unsaturated
compounds
is
a
powerful
methodology
for
the
synthesis
densely
functionalized
five‐membered
heterocyclic
containing
oxygen.
Described
novel
enantioselective
under
Brønsted
base
catalysis.
bis(guanidino)iminophosphorane
as
chiral
organosuperbase
catalyst
enabled
reaction
β
,
γ
‐epoxysulfones
with
imines,
owing
to
its
strong
basicity
high
stereocontrolling
ability,
provide
enantioenriched
1,3‐oxazolidines
having
two
stereogenic
centers,
including
quaternary
one,
in
highly
diastereo‐
manner.
Chemical Reviews,
Journal Year:
2021,
Volume and Issue:
121(11), P. 6373 - 6521
Published: May 21, 2021
The
chiral
oxazoline
motif
is
present
in
many
ligands
that
have
been
extensively
applied
a
series
of
important
metal-catalyzed
enantioselective
reactions.
This
Review
aims
to
provide
comprehensive
overview
the
most
significant
applications
oxazoline-containing
reported
literature
starting
from
2009
until
end
2018.
are
classified
not
by
reaction
which
their
metal
complexes
but
nature
denticity,
chirality,
and
donor
atoms
involved.
As
result,
continued
development
ligand
architectural
design
mono(oxazolines),
bis(oxazolines),
tris(oxazolines)
tetra(oxazolines)
variations
thereof
can
be
more
easily
monitored
reader.
In
addition,
key
transition
states
selected
asymmetric
transformations
will
given
illustrate
features
give
rise
high
levels
induction.
further
aid
reader,
we
summarize
majority
schemes
with
representative
examples
highlight
variation
%
yields
ees
for
carefully
substrates.
should
particular
interest
experts
field
also
serve
as
useful
point
new
researchers
this
area.
It
hoped
stimulate
both
development/design
novel
transformations.
Angewandte Chemie International Edition,
Journal Year:
2018,
Volume and Issue:
57(32), P. 10338 - 10342
Published: June 24, 2018
The
first
example
of
(3+3)-annulation
two
different
three-membered
rings
is
reported
herein.
Donor-acceptor
cyclopropanes
in
reaction
with
diaziridines
were
found
to
afford
perhydropyridazine
derivatives
high
yields
and
diastereoselectivity
under
mild
Lewis
acid
catalysis.
disclosed
applicable
for
the
broad
substrate
scope
exhibits
an
excellent
functional
group
tolerance.
Journal of the American Chemical Society,
Journal Year:
2018,
Volume and Issue:
140(49), P. 17211 - 17217
Published: Nov. 13, 2018
The
first
Lewis
acid
catalyzed
stereoconvergent
transformation
of
racemic
2-(hetero)aryl-N-sulfonylaziridines
via
C–N
bond
cleavage
with
nucleophiles
is
presented.
This
includes
the
[3
+
2]
annulations
(hetero)aromatic
aldehydes
and
1,3-disubstituted
indoles,
asymmetric
Friedel–Crafts
type
reaction
electron-rich
(hetero)arenes,
aminolysis
amines,
providing
facile
access
to
chiral
1,3-isoxazolidines,
pyrroloindolines,
2-(hetero)arylphenethylamines,
vicinal
diamines.
method
features
a
simple
cheaply
available
complex
Cu(I)–chiral
BINAP
catalyst,
excellent
yield
high
diastereo-
enantioselectivities,
mild
conditions.
A
mechanism
involving
I
dynamic
kinetic
transformations
(DyKATs)
aziridines
proposed
based
on
results
control
experiments.
Angewandte Chemie International Edition,
Journal Year:
2018,
Volume and Issue:
57(21), P. 6299 - 6303
Published: April 12, 2018
Abstract
The
formal
[3+2]
cycloaddition
of
epoxides
and
unsaturated
compounds
is
a
powerful
methodology
for
the
synthesis
densely
functionalized
five‐membered
heterocyclic
containing
oxygen.
Described
novel
enantioselective
under
Brønsted
base
catalysis.
bis(guanidino)iminophosphorane
as
chiral
organosuperbase
catalyst
enabled
reaction
β
,
γ
‐epoxysulfones
with
imines,
owing
to
its
strong
basicity
high
stereocontrolling
ability,
provide
enantioenriched
1,3‐oxazolidines
having
two
stereogenic
centers,
including
quaternary
one,
in
highly
diastereo‐
manner.
Angewandte Chemie,
Journal Year:
2018,
Volume and Issue:
130(32), P. 10495 - 10499
Published: June 24, 2018
Abstract
The
first
example
of
(3+3)‐annulation
two
different
three‐membered
rings
is
reported
herein.
Donor‐acceptor
cyclopropanes
in
reaction
with
diaziridines
were
found
to
afford
perhydropyridazine
derivatives
high
yields
and
diastereoselectivity
under
mild
Lewis
acid
catalysis.
disclosed
applicable
for
the
broad
substrate
scope
exhibits
an
excellent
functional
group
tolerance.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(8), P. 2593 - 2596
Published: April 3, 2019
An
efficient
iron
porphyrin
Lewis
acid-catalyzed
cycloaddition
of
aziridines
with
aldehydes
has
been
developed
to
provide
oxazolidines
high
regio-
and
diastereoselectivity.
The
proceeds
in
toluene
1
mol
%
the
catalyst
at
25
°C.
A
theoretical
study
synchrotron-based
X-ray
absorption
fine
structure
measurements
provided
fundamental
insights
into
aziridine–iron
complex,
which
is
key
intermediate
for
generation
1,3-dipole
synthon.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(25), P. 3441 - 3444
Published: Jan. 1, 2024
A
Zn(
ii
)-catalyzed
(3+2)-annulation
of
diaziridines
with
DA
aziridines
has
been
accomplished
via
1,4-hydride
shift
to
furnish
imidazo[1,5-
b
]pyrazole-4,4-dicarboxylates
under
mild
reaction
conditions.
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
88(2), P. 1113 - 1127
Published: Dec. 29, 2022
The
first
organocatalytic
asymmetric
[3
+
2]-annulation
of
γ-sulfonamido-α,β-unsaturated
ketones
with
cyclic
N-sulfimines
has
been
developed,
and
enantioenriched
functionalized
polyheterotricyclic
imidazolidines
were
obtained
in
good
yields
excellent
enantioselectivities.
This
approach
was
also
extended
to
the
γ-hydroxy-α,β-unsaturated
ketones,
affording
oxazolidines.
In
addition,
base-catalyzed
2]-annulations
γ-sulfonamido/γ-hydroxy-α,β-unsaturated
re-investigated
under
mild
reaction
conditions
for
synthesis
racemic
oxazolidines
diastereoselectivities.
