Angewandte Chemie,
Год журнала:
2022,
Номер
135(1)
Опубликована: Ноя. 9, 2022
Abstract
We
report
herein
the
first
examples
of
chiral
phosphoric
acid‐catalyzed
enantioselective
Diels–Alder
reactions
between
2‐trifluoroacetamido‐1,3‐dienes
1
and
α,β‐unsaturated
carbonyl
compounds
2
.
Polysubstituted
1‐acetamido
cyclohexenes
3
were
formed
in
high
yields
with
excellent
diastereo‐
enantioselectivities.
The
reaction
proceeds
through
a
stepwise
process
as
shown
by
deuterium
labelling
experiments.
A
catalytic
three‐component
,
ortho
‐hydroxybenzhydryl
alcohols
4
was
subsequently
developed
furnishing
densely
functionalized
hexahydroxanthenes
5
highly
stereoselective
manner.
This
multicomponent
generates
four
chemical
bonds
concurrent
creation
five
contiguous
stereocenters.
Journal of the American Chemical Society,
Год журнала:
2023,
Номер
145(48), С. 26504 - 26515
Опубликована: Ноя. 27, 2023
Conjugated
trienes
are
fascinating
building
blocks
for
the
rapid
construction
of
complex
polycyclic
compounds.
However,
limited
success
has
been
achieved
due
to
challenging
regioselectivity
control.
Herein,
we
report
an
enantio-
and
diastereoselective
process
allowing
regioselectively
control
functionalization
NH-triene-carbamates.
Synthesis
chiral
cis-3,6-dihydro-2H-1,2-oxazines
is
by
a
phosphoric
acid
catalyzed
Nitroso-Diels-Alder
cycloaddition
involving
[(1E,3E,5E)-hexa-1,3,5-trien-1-yl]carbamates.
Moreover,
modular
access
three
different
regioisomers
with
excellent
diastereoselectivities
high
enantioselectivities
obtained
careful
choice
reaction
conditions.
A
computational
study
reveals
that
influenced
steric
demand
substituents
at
6-position
triene,
as
well
noncovalent
interactions
between
two
partners.
Utility
each
regioisomeric
cycloadduct
highlighted
variety
synthetic
transformations.
Chemical Communications,
Год журнала:
2022,
Номер
58(54), С. 7515 - 7518
Опубликована: Янв. 1, 2022
A
facile
chiral
phosphoric-acid
catalyzed
asymmetric
inverse-electron-demand
aza-Diels-Alder
reaction
of
1,3-diazadienes
with
3-vinylindoles
was
established.
By
using
this
mild
and
practical
protocol,
a
broad
range
benzothiazolopyrimidines
three
contiguous
stereogenic
centers
were
prepared
in
good
yields
excellent
diastereo-
enantio-selectivities
(43
examples,
up
to
83%
yield,
>99%
ee
all
>20
:
1
dr).
plausible
concerted
pathway
enabled
by
the
dual
hydrogen-bonding
effect
proposed
account
for
observed
enantioselectivity
specific
trans-trans
diastereoselectivity.
Organic Letters,
Год журнала:
2023,
Номер
25(28), С. 5395 - 5399
Опубликована: Июль 10, 2023
A
highly
enantioselective
formal
(4
+
2)-cycloaddition
between
carboxylic
acids
and
thiochalcones
promoted
by
(+)-HBTM-2.1
isothiourea
organocatalyst
has
been
reported.
The
methodology
relied
on
the
generation
of
C1-ammonium
enolate
intermediates
proceeded
through
a
nucleophilic
1,4-addition-thiolactonization
cascade.
It
enabled
stereocontrolled
preparation
sulfur-containing
δ-thiolactones
in
good
yields,
moderate
diastereoselectivity,
excellent
enantiomeric
excess
(up
to
99%).
This
annulation
benefited
from
peculiar
reactivity
uncommon
electron-rich
used
as
Michael
acceptors.
European Journal of Organic Chemistry,
Год журнала:
2022,
Номер
2022(34)
Опубликована: Авг. 1, 2022
Abstract
Asymmetric
cycloaddition/annulation
reactions
have
contributed
greatly
to
the
synthesis
of
a
variety
novel
cyclic
compounds
used
in
organic
synthesis,
natural
product
material
science,
and
chemical
biology.
Thus,
chiral
phosphoric
acid‐catalyzed
asymmetric
cycloaddition
received
attention
synthetic
community
design
new
vital
synthesize
complex
molecules
for
past
two
decades.
Although
several
review
articles
on
organocatalyzed
can
be
found
literature,
there
has
been
no
specific
CPA‐catalyzed
reactions.
Herein,
most
recent
research
progress
acid
catalyzed
[3+2],
[4+2],
[2+2],
[3+3],
[4+3],
[4+1]
annulation,
1,3‐dipolar
cycloadditions
compiled
analyzed
demonstrate
importance
catalysis
or
annulation
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
62(1)
Опубликована: Ноя. 9, 2022
We
report
herein
the
first
examples
of
chiral
phosphoric
acid-catalyzed
enantioselective
Diels-Alder
reactions
between
2-trifluoroacetamido-1,3-dienes
1
and
α,β-unsaturated
carbonyl
compounds
2.
Polysubstituted
1-acetamido
cyclohexenes
3
were
formed
in
high
yields
with
excellent
diastereo-
enantioselectivities.
The
reaction
proceeds
through
a
stepwise
process
as
shown
by
deuterium
labelling
experiments.
A
catalytic
three-component
1,
2
ortho-hydroxybenzhydryl
alcohols
4
was
subsequently
developed
furnishing
densely
functionalized
hexahydroxanthenes
5
highly
stereoselective
manner.
This
multicomponent
generates
four
chemical
bonds
concurrent
creation
five
contiguous
stereocenters.
Beilstein Journal of Organic Chemistry,
Год журнала:
2024,
Номер
20, С. 3221 - 3255
Опубликована: Дек. 10, 2024
Asymmetric
cycloaddition
is
a
straightforward
strategy
which
enables
the
synthesis
of
structurally
distinct
cyclic
derivatives
are
difficult
to
access
by
other
methodologies,
using
an
efficient
and
atom-economical
path
from
simple
precursors.
In
recent
years
several
asymmetric
catalytic
cyclization
strategies
have
been
accomplished
for
construction
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(26), С. 5413 - 5418
Опубликована: Янв. 1, 2023
An
inverse-electron-demand
aza-Diels–Alder
reaction
between
4,4-dicyano-2-methylenebut-3-enoates
and
1,3,5-triazinanes
under
catalyst-free
additive-free
conditions
was
developed.
Organic Letters,
Год журнала:
2023,
Номер
25(51), С. 9164 - 9169
Опубликована: Дек. 14, 2023
We
describe
here
an
organocatalytic
asymmetric
cascade
formal
[3
+
3]
cycloaddition
of
benzothiazoles
with
2-nitroallylic
acetates
and
nitroenynes.
This
dearomative
methodology
provided
a
facile
efficient
strategy
for
the
construction
broad
range
valuable
benzothiazolopyridines
bearing
two
adjacent
stereogenic
centers
in
moderate
to
good
yields
excellent
stereocontrol.
RSC Advances,
Год журнала:
2022,
Номер
12(44), С. 28295 - 28298
Опубликована: Янв. 1, 2022
A
simple
and
practical
method
for
the
construction
of
1,3,5-trisubstituted
imidazolidine
derivatives
via
[3
+
2]
cycloaddition
reaction
has
been
developed.
This
could
smoothly
proceed
between
nonstabilized
azomethine
ylides
generated
in
situ
2-benzothiazolamines
to
deliver
a
wide
scope
differently
substituted
imidazolidines
high
yields
(up
98%).
The
structure
one
example
was
confirmed
by
X-ray
single-crystal
analysis.
