Organic Chemistry Frontiers,
Journal Year:
2021,
Volume and Issue:
8(13), P. 3469 - 3474
Published: Jan. 1, 2021
A
chiral
phosphoric
acid-catalyzed
enantioselective
1,6-conjugate
addition
of
thiolacetic
acid
to
alkynyl
indole
imine
methide
in
situ
formed
from
α-(3-indolyl)
propargylic
alcohol
has
been
established.
Advanced Synthesis & Catalysis,
Journal Year:
2021,
Volume and Issue:
363(11), P. 2723 - 2739
Published: April 7, 2021
Abstract
Indole
is
one
of
the
most
important
heterocycles
in
organic
synthesis,
natural
products,
and
drug
discovery.
Recently,
tremendous
advances
selective
functionalization
indoles
have
been
reported.
Although
powered
by
transition
metal
catalysis,
exceedingly
useful
methods
absence
metals
also
In
this
review,
we
provide
an
overview
reactions
that
published
last
years
with
a
focus
on
recent
advances,
aims,
future
trends.
The
review
organized
positional
selectivity
type
used
for
functionalization.
particular,
discuss
major
transition‐metal‐catalyzed
C−H
at
classical
C2/C3
positions,
remote
C4/C7
cross‐coupling,
transition‐metal‐free
magnified
image
Angewandte Chemie International Edition,
Journal Year:
2020,
Volume and Issue:
59(39), P. 17049 - 17054
Published: June 18, 2020
An
organocatalytic
enantioconvergent
synthesis
of
chiral
tetrasubstituted
allenes
is
disclosed.
With
suitable
phosphoric
acid
catalysts,
a
range
racemic
indole-substituted
propargylic
alcohols
reacted
with
nucleophiles
to
provide
efficient
access
series
enantioenriched
high
enantioselectivities.
Control
experiments
suggested
mechanism
involving
remotely
controlled
asymmetric
1,8-addition
the
in
situ
generated
indole
imine
methide
via
bifunctional
transition
state.
Angewandte Chemie International Edition,
Journal Year:
2021,
Volume and Issue:
60(52), P. 27164 - 27170
Published: Oct. 21, 2021
Described
herein
is
a
novel
Brønsted
acid
catalyzed
intramolecular
hydroalkoxylation/Claisen
rearrangement,
allowing
the
practical
and
atom-economic
synthesis
of
range
valuable
spirolactams
from
readily
available
ynamides
in
generally
good
to
excellent
yields
with
diastereoselectivities
broad
substrate
scope.
Importantly,
an
unexpected
dearomatization
nonactivated
arenes
heteroaromatic
compounds
involved
this
tandem
sequence.
Moreover,
asymmetric
version
cyclization
was
also
achieved
by
efficient
kinetic
resolution
chiral
phosphoric
catalysis.
In
addition,
[3,3]-rearrangement
shown
be
kinetically
preferred
over
related
[1,3]-rearrangement
theoretical
calculations.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(7), P. 1212 - 1222
Published: March 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
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(24)
Published: March 25, 2022
Catalytic
asymmetric
synthesis
of
chiral
endocyclic
allenes
remains
a
challenge
in
allene
chemistry
owing
to
unfavored
tension
and
complex
chirality.
Here,
we
present
new
relay
strategy
merging
Pd-catalyzed
[3+2]
annulation
with
enyne-Cope
rearrangement,
providing
facile
route
9-membered
high
efficiency
enantioselectivity.
Moreover,
theoretical
calculations
experimental
studies
were
performed
illustrate
the
critical,
but
unusual
Cope
rearrangement
that
allows
for
complete
central-to-axial
chirality
transfer.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(31)
Published: June 1, 2023
The
skeletons
of
chiral
tetrasubstituted
allenes
bearing
a
vicinal
all-carbon
quaternary
stereocenter
are
importance
but
still
challenging
to
synthesize.
Herein,
we
report
enantio-
and
diastereoselective
γ-additions
1-alkynyl
ketimines
with
dual-copper-catalysis
under
mild
conditions,
affording
α-amino
allenoates
in
high
yields
(up
99
%
yield)
excellent
enantioselectivities
ee)
diastereoselectivities
>20
:
1
dr).
Importantly,
the
stereodivergent
synthesis
products
was
realized
by
asymmetric
γ-addition
reaction
Grignard
reagent
promoted
epimerization.
Moreover,
dual-copper-catalyzed
reactions
were
smoothly
applied
gram-scale
adopted
introduce
allenyl
moieties
into
bioactive
molecules.
Mechanistic
experiments
density
functional
theory
(DFT)
calculations
demonstrated
that
catalyzed
double
copper
catalysts.
Chemical Society Reviews,
Journal Year:
2024,
Volume and Issue:
53(22), P. 11165 - 11206
Published: Jan. 1, 2024
This
review
explores
the
fascinating
world
of
molecules
featuring
multiple
stereogenic
elements,
unraveling
different
strategies
designed
over
years
for
their
enantioselective
synthesis.
