Organic Letters,
Год журнала:
2023,
Номер
25(5), С. 738 - 743
Опубликована: Янв. 30, 2023
Efficient
Ni/(S,S)-Ph-BPE-catalyzed
asymmetric
hydrogenation
of
α-substituted
α,β-unsaturated
phosphine
oxides/phosphonates/phosphoric
acids
has
been
successfully
developed,
and
a
wide
range
chiral
phosphines
products
were
obtained
in
generally
high
yields
with
excellent
enantioselective
control
(92%–99%
yields,
84%−>99%
ee).
This
method
features
cheap
transition
metal
nickel
catalytic
system,
functional
group
tolerance,
substrate
scope
generality,
enantioselectivity.
A
plausible
cycle
was
proposed
for
this
according
to
the
results
deuterium-labeling
experiments.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(15)
Опубликована: Фев. 7, 2023
This
study
establishes
the
first
organocatalytic
enantioselective
synthesis
of
axially
chiral
N,N'-bisindoles
via
phosphoric
acid-catalyzed
formal
(3+2)
cycloadditions
indole-based
enaminones
as
novel
platform
molecules
with
2,3-diketoesters,
where
de
novo
indole-ring
formation
is
involved.
Using
this
new
strategy,
various
were
synthesized
in
good
yields
and
excellent
enantioselectivities
(up
to
87
%
yield
96
ee).
More
importantly,
class
exhibited
some
degree
cytotoxicity
toward
cancer
cells
was
derived
into
phosphine
ligands
high
catalytic
activity.
provides
a
strategy
for
using
asymmetric
organocatalysis
realize
applications
such
scaffolds
medicinal
chemistry
catalysis.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(37)
Опубликована: Июнь 24, 2023
Catalytic
asymmetric
construction
of
chiral
indole-fused
rings
has
become
an
important
issue
in
the
chemical
community
because
significance
such
scaffolds.
In
this
work,
we
have
accomplished
first
catalytic
(4+2)
and
(4+3)
cycloadditions
2,3-indolyldimethanols
by
using
indoles
2-naphthols
as
suitable
reaction
partners
under
catalysis
phosphoric
acids,
constructing
enantioenriched
six-membered
seven-membered
high
yields
with
excellent
enantioselectivities.
addition,
approach
is
used
to
realize
enantioselective
challenging
tetrahydroindolocarbazole
scaffolds,
which
are
found
show
promising
anticancer
activity.
More
importantly,
theoretical
calculations
pathways
activation
mode
offer
in-depth
understanding
class
indolylmethanols.
This
work
not
only
settles
challenges
realizing
indolyldimethanols
but
also
provides
a
powerful
strategy
for
rings.
Precision Chemistry,
Год журнала:
2024,
Номер
2(5), С. 208 - 220
Опубликована: Апрель 23, 2024
The
catalytic
asymmetric
diastereodivergent
synthesis
of
axially
chiral
2-alkenylindoles
was
established
via
phosphoric
acid-catalyzed
addition
reactions
C3-unsubstituted
with
Chinese Journal of Chemistry,
Год журнала:
2021,
Номер
39(8), С. 2163 - 2171
Опубликована: Апрель 29, 2021
Main
observation
and
conclusion
Atroposelective
construction
of
axially
chiral
alkene‐heteroaryl
scaffolds
is
highly
desired
but
challenging.
In
this
work,
we
established
an
atroposelective
alkene‐indole
via
the
strategy
catalytic
enantioselective
addition
reaction
3‐alkynyl‐2‐indolylmethanols
with
bulky
nucleophiles.
strategy,
α‐amido
sulfones
were
used
as
competent
nucleophiles
phosphoric
acid
(CPA)
acted
suitable
catalyst
for
reaction.
By
a
new
class
acyclic
alkene‐indoles
was
synthesized
in
overall
high
yields
(up
to
86%),
excellent
(
E
/
Z
)‐selectivity
(all
>
95
:
5)
good
enantioselectivities
92
8
er).
This
represents
first
frameworks,
which
will
add
member
family
atropoisomeric
heterocycles,
especially
indole
compounds.
Chinese Journal of Organic Chemistry,
Год журнала:
2022,
Номер
42(10), С. 3351 - 3351
Опубликована: Янв. 1, 2022
Indole-based
chiral
heterocycles
constitute
a
class
of
important
heterocyclic
compounds
that
are
found
in
numerous
natural
products,
pharmaceuticals,
pesticide,
and
functional
materials.The
efficient
highly
enantioselective
synthesis
indole
derivatives
has
become
one
the
most
issues
organic
chemistry.Due
to
simple
reactivity
traditional
indoles,
their
involved
catalytic
asymmetric
reactions
very
limited,
resulting
limited
types
constructed
indole-based
frameworks.To
solve
these
challenging
issues,
chemists
devised
strategy
introducing
groups
ring,
so
as
obtain
series
functionalized
derivatives,
namely
platform
molecules,
building
blocks
for
constructing
indole-related
frameworks.Among
them,
2-indolylmethanols
which
were
designed
on
consideration
introduction
hydroxymethyl
group
C2-position
ring
would
change
reactive
site
ring.This
molecules
can
act
either
electrophiles
or
nucleophiles,
multi-carbon
reactions.Therefore,
design
development
have
provided
new
derivatives.The
advances
using
summarized,
will
open
window
designing
application
molecules.
Chinese Journal of Chemistry,
Год журнала:
2022,
Номер
41(1), С. 27 - 36
Опубликована: Сен. 16, 2022
Comprehensive
Summary
A
new
class
of
m
‐hydroxybenzyl
alcohols
has
been
designed
as
competent
three‐carbon
building
blocks
and
achieved
their
application
in
2‐indolylmethanol‐involved
regioselective
(3
+
3)
cycloadditions
under
the
catalysis
Brønsted
acids.
By
this
appoach,
a
series
indole‐fused
six‐membered
cycloadducts
have
synthesized
overall
good
yields
(up
to
98%)
with
excellent
regioselectivity
(all
>95:
5
rr),
thus
affording
powerful
method
for
construction
rings.
Moreover,
catalytic
asymmetric
version
cycloaddition
preliminarily
investigated,
which
revealed
potential
reaction
constructing
chiral
rings
an
enantioselective
manner.
This
work
not
only
accomplished
first
design
reactants,
but
also
represents
cycloadditions.
In
addition,
provides
example
C3‐nucleophilic
2‐indolylmethanols,
will
substantially
enrich
chemistry
2‐indolylmethanols.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(17), С. 3477 - 3502
Опубликована: Янв. 1, 2023
This
review
article
presents
an
in-depth
analysis
of
the
strategies
and
methodologies
for
using
chiral
phosphoric
acids
as
organocatalysts
in
asymmetric
syntheses
from
recent
literature.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
63(8)
Опубликована: Дек. 29, 2023
Abstract
In
the
chemistry
community,
catalytic
asymmetric
synthesis
of
furan‐based
compounds
bearing
both
axial
and
central
chirality
has
proven
to
be
a
significant
but
challenging
issue
owing
importance
difficulty
in
constructing
such
frameworks.
this
work,
we
have
realized
first
five‐five‐membered
via
organocatalytic
(2+4)
annulation
achiral
furan‐indoles
with
2,3‐indolyldimethanols
uncommon
regioselectivity.
By
strategy,
furan‐indole
were
synthesized
high
yields
excellent
regio‐,
diastereo‐,
enantioselectivities.
Moreover,
theoretical
calculations
conducted
provide
an
in‐depth
understanding
reaction
pathway,
activation
mode,
origin
selectivity.
