Abstract
An
acid‐catalyzed,
biomimetic
cascades
strategy
for
the
synthesis
of
proanthocyanidin
analogues
is
reported.
The
method
lays
in
structural
transformations
2‐hydroxychalcone
strongly
affecting
by
pH
and
situ
generated
flavylium
salt
intermediate
could
facile
couping
with
π
‐nucleophile
to
form
proanthocyanidin‐type
product.
A
proposed
bioinspired
cascade
reaction
pathway
based
on
control
experiments
were
also
provided.
These
results
are
interest
developing
total
natural
products.
Organic & Biomolecular Chemistry,
Год журнала:
2021,
Номер
19(18), С. 3960 - 3982
Опубликована: Янв. 1, 2021
Bridged
polycycles
are
privileged
molecular
skeletons
with
wide
occurrence
in
bioactive
natural
products
and
pharmaceuticals.
Therefore,
they
have
been
the
pursing
target
molecules
of
numerous
chemists.
The
rapid
convenient
generation
sp3-rich
complex
three-dimensional
from
simple
easily
available
aromatics
has
made
dearomatization
a
highly
valuable
synthetic
tool
for
construction
rigid
challenging
bridged
rings.
This
review
summarizes
the-state-of-the-art
advances
strategies
application
ring
formation,
discusses
their
advantages
limitations
in-depth
mechanism,
highlights
value
total
synthesis
products.
We
wish
this
will
provide
an
important
reference
medicinal
chemists
inspire
further
development
intriguing
research
area.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(5), С. 1314 - 1321
Опубликована: Янв. 1, 2024
A
new
class
of
chiral
bipyridine-2NO
ligands,
which
incorporate
the
advantages
both
bipyridine
skeleton
and
pyrroloimidazolone-based
N
-oxide
moiety,
was
developed.
New Journal of Chemistry,
Год журнала:
2024,
Номер
48(4), С. 1688 - 1695
Опубликована: Янв. 1, 2024
This
work
diversified
the
Py-2NO
ligand
library
recently
developed
by
our
group
and
further
expanded
application
of
chiral
ligands
in
asymmetric
catalysis.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(13), С. 1474 - 1480
Опубликована: Март 1, 2024
Comprehensive
Summary
The
privileged
C
2
‐symmetric
rigid
phenol‐type
ligand
is
more
attractive
but
challenging
in
asymmetric
catalysis.
Herein,
we
designed
and
synthesized
a
class
of
rigid‐featured
chiral
tridentate
Phenol‐2NO
ligands,
that
incorporate
the
advantages
both
phenol
skeleton
pyrroloimidazolone‐based
N
‐oxide
moiety,
from
readily
available
L
‐prolinamides
operationally
simple
two
steps
up
to
44%
overall
yield.
More
importantly,
using
an
achiral
quinoline
derivative
as
additive,
newly
developed
could
serve
anioic
upon
deprotonative
activation
coordinate
Zn(II)
form
highly
enantioselective
catalyst
for
Michael‐type
Friedel‐Crafts
alkylation
reaction
indoles
with
2,3‐dioxopyrrolidines.
Excellent
yields
(up
90%)
high
enantioselectivities
99%
ee)
are
obtained
wide
range
substrates
under
mild
conditions.
Experiments
DFT
calculations
revealed
mechanism
origins
enantioselectivity.
This
also
represented
first
ligand/metal
complex
by
organic
base
additive
The Journal of Organic Chemistry,
Год журнала:
2019,
Номер
84(12), С. 7883 - 7893
Опубликована: Май 28, 2019
A
BINOL-based
chiral
phosphoric
acid
was
employed
as
an
efficient
catalyst
in
enantioselective
cycloaddition
of
ortho-hydroxyphenyl-substituted
para-quinone
methides
and
enamides,
which
gave
rise
to
acetamido-substituted
tetrahydroxanthenes
with
three
adjacent
stereogenic
centers
high
yields
(up
99%)
excellent
stereoselectivities
>99:1
diastereomeric
ratio
up
98%
ee).
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(19), С. 5306 - 5357
Опубликована: Янв. 1, 2022
The
review
highlights
the
transition
metal-free
methodologies
developed
for
synthesising
various
heterocyclic
compounds
by
utilising
α,β
-unsaturated
ketones
as
valuable
synthons
during
period
of
2009
to
2020.
Chemical Communications,
Год журнала:
2019,
Номер
55(36), С. 5207 - 5210
Опубликована: Янв. 1, 2019
An
unexpected
multi-component
one-pot
cascade
reaction
of
hydroxyketones
with
ortho-hydroxychalcones
has
been
developed
to
afford
an
array
new
furanobenzopyran-fused
polycyclic
compounds
complex
molecular
architectures.
This
not
only
establishes
a
mode
but
also
provides
expedient
and
convenient
synthetic
strategy
access
heterocycles.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(42)
Опубликована: Авг. 19, 2023
Abstract
To
expand
the
chemical
space
of
chiral
N
‐oxides
and
furan‐containing
ligands,
herein
we
designed
synthesized
a
new
class
rigid‐featured
tertiary
amine‐derived
C
2
‐symmetric
furan‐
,
N′
‐dioxide
(Fu‐2NO)
ligands
from
optically
pure
l
‐prolinamides/hydroxylprolinamides
in
operationally
simple
two
steps
up
to
57
%
overall
yield.
The
newly
developed
Fu‐2NO
possesses
pyrroloimidazolone‐based
as
non‐flat
walls,
afforded
opportunity
for
fine‐tuning
ligand
electronic
conformational
properties
by
judicious
choice
substituent
nonligating
nitrogen
atom.
More
importantly,
can
tolerate
air
moisture
such
that
no
special
handling
is
needed
their
storage,
be
applied
Ni(II)‐catalyzed
asymmetric
Friedel‐Crafts
alkylation
reaction
indole.
Advanced Synthesis & Catalysis,
Год журнала:
2018,
Номер
361(3), С. 456 - 461
Опубликована: Ноя. 10, 2018
Abstract
The
first
p
‐TSA‐catalyzed
highly
diastereoselective
Michael
addition/cyclization
of
3‐carboxylate‐substituted
isoindolinones
and
ortho
‐hydroxychalcones
was
developed
to
access
a
wide
range
chroman‐bridged
polycyclic
isoindolinones.
This
reaction
represents
novel
efficient
method
for
the
construction
complex
bridged
Moreover,
several
derivatizations
were
carried
out
further
highlight
synthetic
value
this
protocol.
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