Asian Journal of Organic Chemistry,
Год журнала:
2022,
Номер
11(9)
Опубликована: Июль 26, 2022
Abstract
A
chiral
phosphoric
acids
catalyzed
regio‐
and
enantioselective
1,10‐conjugate
addition
of
2‐arylindoles
to
alkynyl
indole
imine
methides
formed
in
situ
from
α‐(6‐indolyl)propargylic
alcohols
has
been
developed.
With
the
established
system,
organocatalytic
asymmetric
3‐allenylation
indoles
was
realized,
affording
a
broad
scope
axially
tetrasubstituted
allenes
bearing
two
motifs
high
yields
with
stereoselectivities.
Importantly,
remote
stereocontrolled
strategy
disclosed
via
for
first
time.
Advanced Synthesis & Catalysis,
Год журнала:
2022,
Номер
364(7), С. 1212 - 1222
Опубликована: Март 9, 2022
Abstract
Axially
chiral
allenes
occur
on
a
wide
range
of
natural
products
and
synthetic
molecules
with
significant
biological
activity.
Furthermore,
they
are
versatile
building
blocks
in
organic
synthesis
because
their
inherent
chemical
properties.
Accordingly,
catalytic
enantioselective
axially
has
been
paid
much
attention.
Benefited
from
the
development
asymmetric
organocatalysis,
many
simple
efficient
methods
terms
different
systems
as
well
reaction
partners
have
developed.
This
review
will
focus
recent
progress
field
organocatalytic
(2000–2022),
which
is
organized
according
to
types
catalyst
system
used.
magnified
image
Advanced Synthesis & Catalysis,
Год журнала:
2020,
Номер
363(4), С. 852 - 876
Опубликована: Ноя. 18, 2020
Abstract
Heterocyclic
compounds
are
important
organic
and
have
emerged
as
key
scaffolds
in
numerous
drugs,
natural
products,
vitamins,
biologically
pharmaceutically
active
compounds.
Over
the
past
few
decades,
development
of
versatile
methodologies
employing
propargylic
alcohols
synthons
for
construction
heterocyclic
skeletons
has
attracted
great
attention
from
synthetic
chemists.
In
this
review,
recent
developments
cascade
cyclization
with
diverse
nucleophiles
to
construct
summarized.
According
types
nucleophiles,
these
reactions
can
be
divided
into
four
categories:
1)
Reactions
involving
C‐nucleophiles
capture
allenyl
carbocation;
2)
O,
S‐nucleophiles
3)
N,
P‐nucleophiles
4)
halo‐nucleophiles
carbocation.
magnified
image
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(5), С. 1234 - 1240
Опубликована: Янв. 1, 2022
Chiral
phosphoric
acid
has
been
utilized
for
covalent
activation
of
propargylic
alcohols
to
act
as
pre-catalyst.
With
this
mode,
a
range
highly
regio-
and
enantioenriched
heterocyclic
products
could
be
generated
efficiently
from
racemic
alcohols.
Organic Letters,
Год журнала:
2022,
Номер
24(27), С. 4914 - 4918
Опубликована: Июнь 30, 2022
An
asymmetric
organocatalytic
remote
1,10-addition
of
alkynyl
indole
imine
methides
generated
in
situ
from
α-(6-indolyl)
propargylic
alcohols
with
thiazolones
has
been
developed
for
the
first
time,
affording
axially
chiral
tetrasubstituted
allenes
featuring
vicinal
sulfur-containing
quaternary
carbon
stereocenters
high
yields
excellent
stereoselectivities.
The
representative
scale-up
reaction
and
transformations
1,10-adduct
were
examined.
mechanism
was
expounded
by
control
experiments
DFT
calculations.
European Journal of Organic Chemistry,
Год журнала:
2022,
Номер
2022(7)
Опубликована: Фев. 17, 2022
Abstract
It
is
only
in
the
two
last
decades
that
first
examples
of
organocatalytic
dynamic
kinetic
resolutions
(DKRs)
have
been
disclosed.
These
methodologies
allow
resolving
racemic
compounds
with
up
to
quantitative
yield.
Today,
a
variety
chiral
organocatalysts
are
capable
providing
excellent
enantioselectivities
many
types
transformations
evolving
through
DKR.
The
goal
this
review
update
field
DKRs
since
2016.
divided
into
six
sections,
according
different
employed
these
reactions,
such
as
Brønsted
acid
catalysts,
hydrogen‐bonding
N‐heterocyclic
carbene
Lewis
base
phase‐transfer
and
cinchona
alkaloid‐based
catalysts.
Organic Letters,
Год журнала:
2022,
Номер
24(18), С. 3319 - 3324
Опубликована: Май 4, 2022
A
novel
organocatalytic
asymmetric
formal
[3
+
2]
cycloaddition
of
3-substituted
1H-indoles
with
in
situ
generated
3-hydroxy-isoindolinone-derived
β,γ-alkynyl-α-ketimines
has
been
developed.
variety
biologically
relevant
chiral
spiro-isoindolinone-indolines
were
achieved
excellent
yields
(up
to
99%)
and
enantioselectivity
99%
ee)
under
mild
conditions.
The
gram-scale
reaction
this
methodology
several
interesting
transformations
the
products
have
demonstrated.
Journal of the American Chemical Society,
Год журнала:
2023,
Номер
145(26), С. 14562 - 14569
Опубликована: Июнь 21, 2023
Catalytic
enantioselective
construction
of
optically
active
tetraarylmethanes
remains
a
challenging
issue
in
the
field
asymmetric
synthesis
because
overwhelming
steric
hindrance
and
formidable
stereocontrol
that
existed
all-aryl-substituted
quaternary
carbon
stereocenter.
Here,
we
reported
an
organocatalytic
chiral
from
racemic
tertiary
alcohols.
With
aid
phosphoric
acid
catalyst,
6-methylenenaphthalen-2(6H)-ones
were
generated
situ
6-(hydroxydiarylmethyl)naphthalen-2-ols,
followed
by
stereoselective
1,8-conjugate
addition
to
afford
corresponding
high
excellent
yields
with
enantioselectivities.
Furthermore,
scope
alcohols
has
been
successfully
enlarged
6-(hydroxydiphenylmethyl)naphthalen-2-amines.
Notably,
it
is
first
time
use
2-naphthol/naphthalen-2-amine
unit
as
auxiliary
group
generate
α,β,γ,δ,ε,ζ-conjugate
systems,
which
have
involved
remote
stereocontrolled
reactions.
Particularly,
stereoconvergent
formal
nucleophilic
substitution
reaction
triarylmethanols
achieved
for
tetraarylmethanes.
In
addition,
DFT
calculations
applied
provide
guidance
design
additional
understand
origin
stereoselectivity.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(10)
Опубликована: Янв. 9, 2024
Abstract
We
present
the
first
example
of
electrocatalytic
three‐component
annulation–iodosulfonylation
indole‐tethered
1,6‐enynes
with
arylsulfonyl
hydrazides
and
KI
for
accessing
various
iodosulfonated
pyrrolo[1,2‐
a
]indoles
in
moderate
to
excellent
yields
high
stereospecificity.
This
electrosynthesis
opens
new
avenues
construction
skeleton
good
functional
group
compatibility
under
environmentally
benign
condition.
Based
on
control
experiments
cyclic
voltammetry
data,
we
suggested
plausible
reaction
mechanism
which
included
anodic
oxidation,
homolysis
iodide,
radical
addition,
5
‐
exo
dig
cyclization,
coupling
or
nucleophilic
attack
iodide
ions
cascade.
Organic & Biomolecular Chemistry,
Год журнала:
2021,
Номер
19(35), С. 7544 - 7574
Опубликована: Янв. 1, 2021
This
review
focuses
on
recent
developments
in
the
synthesis
of
pyrrolo[1,2-
a
]indole
derivatives.
The
mechanism,
factors
affecting
yield
and
selectivity
product,
application
to
bioactive
molecules
are
explained.
Organic Letters,
Год журнала:
2022,
Номер
24(35), С. 6472 - 6476
Опубликована: Авг. 30, 2022
Catalyst-controlled
divergent
reactions
of
2,3-disubstituted
indoles
with
propargylic
alcohols
were
developed
for
the
first
time.
In
presence
TsOH
or
B(C6F5)3
as
catalyst,
reacted
smoothly
3-alkynyl-3-hydroxyisoindolinones
to
afford
3H-benzo[b]azepines
by
selective
C2(sp2)-C3(sp2)
ring
expansion
indoles.
contrast,
decreasing
catalyst
strength
(e.g.,
chiral
phosphoric
acid)
interrupted
cascade
reactions,
affording
axially
tetrasubstituted
allenes
bearing
an
adjacent
quaternary
carbon
stereocenter.
Control
experiments
provided
insights
into
reaction
mechanism.
