The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(20), P. 14571 - 14586
Published: Oct. 4, 2023
An
efficient
and
practical
cascade
cyclization
of
1,5-diynols
with
(RO)2P(O)SH
as
the
acid
promoter
nucleophile
under
mild
conditions
was
developed.
A
variety
highly
substituted
benzo[b]fluorenyl-containing
S-alkyl
phosphorothioates
were
successfully
constructed
in
moderate
to
excellent
yields.
Furthermore,
this
protocol
exhibited
good
functional
group
tolerance,
a
broad
substrate
scope,
potential
applications,
water
only
byproduct.
The
reaction
proceeded
allenyl
thiophosphate
key
intermediate,
followed
by
Schmittel-type
process
produce
target
product.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(5), P. 1234 - 1240
Published: Jan. 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,
Journal Year:
2022,
Volume and Issue:
24(27), P. 4914 - 4918
Published: June 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.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(35), P. 6472 - 6476
Published: Aug. 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.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(14), P. 3662 - 3668
Published: Jan. 1, 2023
With
the
aid
of
chiral
phosphoric
acid,
enantioselective
1,6-addition
tryptamines
to
in
situ
formed
alkynyl
7-methylene-7
H
-indoles
from
tertiary
α-(7-indolyl)methanols
has
been
established,
furnishing
axially
tetrasubstituted
allenes
high
yields.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(18), P. 2991 - 3019
Published: July 14, 2023
Abstract
Propargylic
alcohols
are
readily
available
bifunctional
(alkyne
and
hydroxyl
groups)
synthons,
which
recognize
as
one
of
the
attractive
synthetic
feedstock
in
organic
transformations.
Especially,
recent
years
employment
these
valuable
molecules
has
frequently
been
observed
literature.
Hence,
present
review
highlights
advancements
application
propargylic
cyclization,
substitution,
addition
reactions.
Chemistry - A European Journal,
Journal Year:
2021,
Volume and Issue:
27(63), P. 15571 - 15604
Published: Aug. 3, 2021
Oxygen-bearing
motifs,
mainly
the
congener
heterocycles
are
ubiquitous
due
to
their
presence
in
various
natural
products
and
bioactive
scaffolds.
Although
literature,
several
strategies
have
been
developed
for
synthesis,
hydroalkoxylation
of
alkynes
has
come
forward
as
a
method
choice
used
extensively.
In
particular,
gained
enormous
attention
from
synthetic
community
rapid
access
very
useful
reactive
intermediate
like
'enol
ether'.
Furthermore,
manifold
utility
these
methods,
reports
elaborating
generation
ether'
using
usage
reactions
cascade
or
tandem
manner.
This
review
focuses
on
recent
development
synthesis
oxygen-containing
entities.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
20(31), P. 6037 - 6056
Published: Jan. 1, 2022
This
review
article
contains
various
synthetic
strategies
for
the
generation
of
pyridines,
quinolines,
and
isoquinolines
from
propargylic
alcohols
during
period
between
2005–2021.
is
first
focused
that
has
appeared
on
this
topic.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(8), P. 1263 - 1267
Published: Feb. 16, 2023
A
general
and
metal-free
protocol
for
the
construction
of
benzo[b]fluorenyl
thiophosphates
was
developed
through
cascade
cyclization
easily
prepared
diynols
(RO)2P(O)SH,
with
water
as
only
byproduct.
The
novel
transformation
involved
allenyl
thiophosphate
key
intermediate,
followed
by
Schmittel-type
to
achieve
desired
products.
Notably,
(RO)2P(O)SH
acted
not
a
nucleophile
but
also
an
acid-promoter
initiate
reaction.
