Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(8), С. 1185 - 1190
Опубликована: Март 29, 2023
Abstract
Herein
we
disclose
a
catalytic
asymmetric
dearomatization
reaction
of
β‐
naphthols
with
4‐aryl‐1,2,4‐triazole‐3,5‐diones.
A
chiral
phosphoric
acid
spiro
motif
was
found
to
be
effective
for
this
reaction.
The
urazole
embedded
naphthalenones
having
both
axial
and
central
chirality
were
obtained
in
good
high
yields
(70–85%)
diastereo‐
enantioselectivities
(>20:1,
8–96%
ees),
C−N
rotational
energy
barrier
31.54
K.Cal.mol
−1
t
1/2
25
°C=589.8
years.
scope
the
broad
few
applications
including
bromo‐amination
have
been
demonstrated.
magnified
image
Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
364(2), С. 274 - 280
Опубликована: Окт. 21, 2021
Abstract
An
enantioselective
synthesis
of
unnatural
pyrazole‐based
α‐chiral
amino
acid
derivatives
from
the
asymmetric
reaction
N
‐aryl‐5‐aminopyrazoles
with
β,γ‐alkynyl‐α‐imino
esters
using
a
chiral
spirocyclic
phosphoric
catalyst
was
developed.
Using
established
methodology,
various
α‐amino
tetrasubstituted
carbon
stereocenters
were
obtained
in
67–98%
yields
and
73–99%
enantioselectivities.
The
NH
2
functionality
corresponding
products
enables
further
transformations
to
thiourea
lactam.
magnified
image
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
21(2), С. 252 - 272
Опубликована: Дек. 5, 2022
Four
organocatalytic
approaches
for
the
synthesis
of
axially
chiral
tetrasubstituted
allenes
are
described
with
new
critical
insights
into
reaction
scope
and
mechanisms.
Chemical Communications,
Год журнала:
2023,
Номер
60(7), С. 831 - 834
Опубликована: Дек. 15, 2023
We
herein
report
regio-
and
enantioselective
arylation
of
β,γ-alkynyl-α-imino
esters
with
pyrroloisoquinolines.
Using
chiral
phosphoric
acid
catalysts,
a
wide
range
novel
axially
tetrasubstituted
α-amino
allenoates
were
accessed
in
good
yields
excellent
enantioselectivities.
Notably,
this
transformation
occurred
preferentially
at
the
sterically
more
hindered
C1-position
The
potential
scalability
late-stage
functionalization
demonstrated
utility
current
protocol.
Chemical Communications,
Год журнала:
2024,
Номер
60(79), С. 11116 - 11119
Опубликована: Янв. 1, 2024
Herein,
we
report
an
example
of
a
stereoselective
γ-addition
reaction
trifluoromethyl
ketimines
to
1-alkynyl
ketones
mediated
by
isothiourea,
BTM,
under
mild
conditions,
which
afforded
tetrasubstituted
allenes
with
central
chiralities
in
high
yields
(up
94%
yield),
good
enantioselectivities
91%
ee),
and
excellent
diastereoselectivities
(all
>20
:
1
dr).
In
addition,
the
BTM-catalyzed
was
successfully
applied
gram-scale
reaction,
unexpected
benzopyrrolothiazine
derivative
converted,
albeit
racemic.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(8), С. 1185 - 1190
Опубликована: Март 29, 2023
Abstract
Herein
we
disclose
a
catalytic
asymmetric
dearomatization
reaction
of
β‐
naphthols
with
4‐aryl‐1,2,4‐triazole‐3,5‐diones.
A
chiral
phosphoric
acid
spiro
motif
was
found
to
be
effective
for
this
reaction.
The
urazole
embedded
naphthalenones
having
both
axial
and
central
chirality
were
obtained
in
good
high
yields
(70–85%)
diastereo‐
enantioselectivities
(>20:1,
8–96%
ees),
C−N
rotational
energy
barrier
31.54
K.Cal.mol
−1
t
1/2
25
°C=589.8
years.
scope
the
broad
few
applications
including
bromo‐amination
have
been
demonstrated.
magnified
image
