Chemical Science,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
The
previously
unreported
combination
of
nucleophilic
phosphine
catalysis
and
energy
transfer
allows
for
the
rapid
construction
structurally
distinct
2-oxabicyclo[2.1.1]hexanes
(2-oxa-BCH)
from
readily
available
building
blocks
with
high
atom
economy.
Previous
multistep
routes
to
these
important
phenyl
ring
bioisosteres
have
largely
depended
on
use
bespoke
strain-release
agents
or
multiple
post-functionalisation
reactions
access
structural
diversity
scaffold.
In
contrast,
this
cascade
reaction
medicinal
chemist
exploit
breadth
commercial
allyl
alcohols
synthesise
systematically
diverse
2-oxa-BCH
architectures.
Using
a
polar
radical
disconnections
in
same
flask,
every
position
scaffold
can
be
substituted
useful
functional
handles
such
as
protected
amines,
esters
alcohols,
well
arenes
alkyl
groups.
Cyclic
even
employed
yield
single
diastereomers
sp
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 26, 2024
A
palladium-catalyzed
[2π
+
2σ]
cycloaddition
of
vinyl
bicyclo[1.1.0]butanes
with
methyleneindolinones
has
been
developed.
The
reaction
enables
the
construction
spirobicyclo[2.1.1]hexanes
bearing
an
all-carbon
quaternary
center
in
moderate
to
good
yields
excellent
diastereoselectivities.
This
method
features
a
broad
substrate
scope
functional
group
compatibility.
practical
utility
this
protocol
was
further
demonstrated
by
gram-scale
synthesis
and
postsynthetic
transformations
desired
product.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(43)
Published: Aug. 5, 2024
Abstract
Bridged
bicyclic
compounds
(BBCs)
have
recently
emerged
as
effective
3D‐isosteres
of
planar
aryl
and
heteroaryl
rings.
Current
synthetic
endeavours
are
devoted
to
accessing
these
complex
structures
bearing
functionalities
in
different
positions
the
aliphatic
Of
particular
interest
is
incorporation
F‐containing
motifs,
since
it
allows
generation
isosteric
units
with
improved
physicochemical
properties,
including
lipophilicity,
water
solubility,
or
oxidative
resistance.
Chemical Science,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
The
previously
unreported
combination
of
nucleophilic
phosphine
catalysis
and
energy
transfer
allows
for
the
rapid
construction
structurally
distinct
2-oxabicyclo[2.1.1]hexanes
(2-oxa-BCH)
from
readily
available
building
blocks
with
high
atom
economy.
Previous
multistep
routes
to
these
important
phenyl
ring
bioisosteres
have
largely
depended
on
use
bespoke
strain-release
agents
or
multiple
post-functionalisation
reactions
access
structural
diversity
scaffold.
In
contrast,
this
cascade
reaction
medicinal
chemist
exploit
breadth
commercial
allyl
alcohols
synthesise
systematically
diverse
2-oxa-BCH
architectures.
Using
a
polar
radical
disconnections
in
same
flask,
every
position
scaffold
can
be
substituted
useful
functional
handles
such
as
protected
amines,
esters
alcohols,
well
arenes
alkyl
groups.
Cyclic
even
employed
yield
single
diastereomers
sp
