Chemistry - A European Journal,
Год журнала:
2022,
Номер
28(46)
Опубликована: Июнь 2, 2022
Abstract
The
aza‐
ortho
‐quinone
methide
(aza‐
o
‐QM)
chemistry
has
overwhelmingly
progressed
in
the
past
few
decades.
This
review
aims
to
integrate
various
transition
metal‐catalyzed
and
organocatalytic
strategies
taming
aza
‐o‐
QM
intermediates,
including
‐vinylidene
quinone
‐VQM),
‐alkynyl
‐AQM),
para
p
‐QM),
indole‐based
‐QM
analog.
These
transient
species
are
often
utilized
for
direct
enantioselective
synthesis
of
complex
(hetero)polycyclic
or
fused‐ring
molecular
scaffolds
such
as
tetrahydroquinoline
indoline,
among
others,
which
abundant
many
natural
products,
bioactive
compounds,
pharmaceuticals.
Organic Letters,
Год журнала:
2020,
Номер
22(14), С. 5439 - 5445
Опубликована: Июнь 29, 2020
We
report
the
chiral
phosphoric
acid
catalyzed
formal
(3
+
2)
cycloaddition
of
3-substituted
1H-indoles
and
propargylic
alcohols
containing
a
functional
directing
group
(p-NHAc
or
p-OH).
This
work
represents
straightforward
method
to
synthesize
pyrrolo[1,2-a]indole
bearing
tetrasubstituted
carbon
stereocenter.
The
reaction
proceeds
smoothly
with
wide
array
substrate
tolerance
deliver
various
pyrrolo[1,2-a]indoles
in
up
93%
yield
98%
ee.
utility
this
is
highlighted
by
diverse
transformations
products
into
indole
derivatives.
Organic Chemistry Frontiers,
Год журнала:
2021,
Номер
8(13), С. 3469 - 3474
Опубликована: Янв. 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.
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.
Chemistry - A European Journal,
Год журнала:
2022,
Номер
28(46)
Опубликована: Июнь 2, 2022
Abstract
The
aza‐
ortho
‐quinone
methide
(aza‐
o
‐QM)
chemistry
has
overwhelmingly
progressed
in
the
past
few
decades.
This
review
aims
to
integrate
various
transition
metal‐catalyzed
and
organocatalytic
strategies
taming
aza
‐o‐
QM
intermediates,
including
‐vinylidene
quinone
‐VQM),
‐alkynyl
‐AQM),
para
p
‐QM),
indole‐based
‐QM
analog.
These
transient
species
are
often
utilized
for
direct
enantioselective
synthesis
of
complex
(hetero)polycyclic
or
fused‐ring
molecular
scaffolds
such
as
tetrahydroquinoline
indoline,
among
others,
which
abundant
many
natural
products,
bioactive
compounds,
pharmaceuticals.