Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(30)
Published: May 10, 2022
The
success
of
saturated,
fluorinated
heterocycles
in
contemporary
drug
discovery
provides
a
stimulus
for
creative
endeavor
main
group
catalysis.
Motivated
by
the
ubiquity
isochromans
across
bioactive
small
molecule
spectrum,
prominence
anomeric
effect
regulating
conformation,
and
metabolic
lability
benzylic
position,
iodine(I)/iodine(III)
catalysis
has
been
leveraged
stereocontrolled
generation
selectively
analogs.
To
augment
current
arsenal
fluorocyclization
reactions
involving
carboxylic
acid
derivatives,
reaction
readily
accessible
2-vinyl
benzaldehydes
is
disclosed
(up
to
>95
:
05
d.r.
97
03
e.r.).
Key
stereoelectronic
interactions
manifest
themselves
X-ray
crystal
structures
products,
thereby
validating
[CH
Expert Opinion on Drug Discovery,
Journal Year:
2021,
Volume and Issue:
16(11), P. 1261 - 1286
Published: June 2, 2021
Introduction
There
continues
to
be
an
exponential
rise
in
the
number
of
small
molecule
drugs
that
contain
either
a
fluorine
atom
or
fluorinated
fragment.
While
unique
properties
enable
precise
modulation
molecule's
physicochemical
properties,
strategic
bioisosteric
replacement
fragments
with
moieties
represents
area
significant
growth.Areas
covered
This
review
discusses
employment
substitution
design
and
development
bioisosteres
medicinal
chemistry.
In
addition,
classic
exploitation
trifluoroethylamine
group
as
amide
bioisostere
is
discussed.
each
case
studies
presented,
emphasis
placed
on
context-dependent
influence
fragment
overall
properties/binding
compound
interest.Expert
opinion
Whereas
utilization
replacements
modify
molecular
structures
commonplace
within
drug
discovery,
overarching
lesson
learned
chances
success
this
strategy
significantly
increase
knowledge
structure/environment
biological
target
grows.
Coupled
this,
breakthroughs
learnings
achieved
using
specific
program
are
context-based,
though
may
helpful
guiding
future
intuition,
will
not
necessarily
directly
translated
programs.
Another
important
point
bear
mind
what
implications
structural
change
based
have
candidate
molecule.
Finally,
new
methods
reagents
for
controlled
regioselective
introduction
into
biologically
relevant
compounds
particularly
discovery
remains
contemporary
challenge
organic
Journal of the American Chemical Society,
Journal Year:
2021,
Volume and Issue:
143(4), P. 1745 - 1751
Published: Jan. 22, 2021
Metal-free,
catalytic
enantioselective
intermolecular
oxyamination
of
alkenes
is
realized
by
use
organoiodine(I/III)
chemistry.
The
protocol
applicable
toward
aryl-
and
alkyl-substituted
with
high
enantioselectivity
electronically
controlled
regioselectivity.
oxyaminated
products
can
be
easily
deprotected
in
one
step
to
reveal
free
amino
alcohols
yields
without
loss
enantioselectivity.
A
key
our
success
the
discovery
a
virtually
unexplored
chemical
entity,
N-(fluorosulfonyl)carbamate,
as
bifunctional
N,O-nucleophile.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(9)
Published: Jan. 4, 2022
The
generation
of
sulfonyl
radicals
has
long
been
known
as
a
flexible
strategy
in
wide
range
different
sulfonylative
transformations.
Meanwhile
their
use
alkylation
processes
somehow
limited
due
to
inherent
difficulty
evolving
less-stable
after
sulfur
dioxide
extrusion.
Herein
we
report
convenient
that
involves
gem-difluorinated
sulfinates
an
"upgrading-mask",
allowing
these
precursors
decompose
into
corresponding
alkyl
radicals.
electron-donor
character
the
formation
electron
donor-acceptor
(EDA)
complex
with
transient
iminium
ions
is
displayed,
achieving
first
example
stereocontrolled
light-driven
insertion
gem-difluoro
derivatives
unsaturated
aldehydes.
This
methodology
compatible
flow
conditions,
maintaining
identical
levels
enantiocontrol.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(30)
Published: May 10, 2022
The
success
of
saturated,
fluorinated
heterocycles
in
contemporary
drug
discovery
provides
a
stimulus
for
creative
endeavor
main
group
catalysis.
Motivated
by
the
ubiquity
isochromans
across
bioactive
small
molecule
spectrum,
prominence
anomeric
effect
regulating
conformation,
and
metabolic
lability
benzylic
position,
iodine(I)/iodine(III)
catalysis
has
been
leveraged
stereocontrolled
generation
selectively
analogs.
To
augment
current
arsenal
fluorocyclization
reactions
involving
carboxylic
acid
derivatives,
reaction
readily
accessible
2-vinyl
benzaldehydes
is
disclosed
(up
to
>95
:
05
d.r.
97
03
e.r.).
Key
stereoelectronic
interactions
manifest
themselves
X-ray
crystal
structures
products,
thereby
validating
[CH
