Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(47), P. 8397 - 8401
Published: Nov. 20, 2023
We
presented
a
method
for
synthesizing
allylic
chiral
hydrazones
from
1,4-disubstituted
1,3-dienes
and
through
(R)-DTBM-Segphos-Pd(0)-catalyzed
hydrohydrazonation
reaction.
This
transformation
has
wide
range
of
substrates
good
functional
group
tolerance.
The
desired
products
were
obtained
in
medium
to
high
yield
regio-
enantioselectivity.
Synthetic
the
into
various
nitrogen-containing
compounds
was
demonstrated.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(43)
Published: Sept. 15, 2023
Abstract
We
report
herein
a
Cu‐catalyzed
regio‐,
diastereo‐
and
enantioselective
acylboration
of
1,3‐butadienylboronate
with
acyl
fluorides.
Under
the
developed
conditions,
reactions
provide
(
Z
)‐β,γ‐unsaturated
ketones
bearing
an
α‐tertiary
stereocenter
high
‐selectivity
excellent
enantioselectivities.
While
direct
access
to
highly
enantioenriched
E
‐isomers
was
not
successful,
we
showed
that
such
molecules
can
be
synthesized
optical
purities
via
Pd‐catalyzed
alkene
isomerization
from
corresponding
‐isomers.
The
orthogonal
chemical
reactivities
functional
groups
embedded
in
ketone
products
allow
for
diverse
chemoselective
transformations,
which
provides
valuable
platform
further
derivatization.
ACS Catalysis,
Journal Year:
2023,
Volume and Issue:
13(16), P. 10887 - 10894
Published: Aug. 3, 2023
The
practical
synthesis
of
C-stereogenic
α-aminophosphine
oxides,
which
exhibit
a
wide
range
applications
in
medicinal
chemistry,
biochemistry,
material
science,
and
asymmetric
catalysis,
represents
an
unmet
need.
Herein,
Ni/(S,S)-BenzP*
catalyst
system
is
developed
for
branched
oxides
through
enantioselective
Markovnikov
addition
H-phosphine
to
2-azadienes.
A
variety
readily
available
2-azadienes
undergo
hydrophosphinylation
with
high
enantioselectivities
(up
99%)
good
yields
96%).
These
products
can
be
hydrolyzed
afford
synthetically
valuable
chiral
are
key
building
blocks
the
bioactive
compounds
(such
as
phospholeucine
synthesized
herein),
organocatalysts,
ligands.
Mechanistic
studies
suggest
hydrofunctionalization
process.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(22), P. 4177 - 4182
Published: May 30, 2023
A
highly
efficient,
palladium-catalyzed
glycosylation
between
3,4-O-carbonate
glycals
and
acid-labile
oximes
is
disclosed.
This
approach
features
broad
substrate
scope,
high
functional
group
tolerance,
easy
scalability,
delivering
glycosyl
in
excellent
yields
with
exclusive
β-selectivity
retention
of
Z/E
geometries.
The
power
this
method
demonstrated
by
a
set
site-selective
transformations
products
late-stage
glycodiversification
bioactive
molecules.
Overall,
our
strategy
provides
an
efficient
toolkit
for
facile
access
to
valuable
N-O-linked
glycosides.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
26(1), P. 89 - 93
Published: Dec. 21, 2023
Different
from
electronically
matched
1,4-
and
1,6-additions,
herein,
we
disclose
an
mismatched
1,5-conjugate
addition
process
with
oximes
as
the
nucleophiles.
By
this
design,
oxime
moieties
are
readily
introduced
to
γ-position
of
electron-deficient
substrates
in
good
yields,
excellent
regioselectivities,
high
enantioselectivities.
The
corresponding
allyl
also
conveniently
transformed
into
a
series
valuable
enantioenriched
skeletons.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(47), P. 8397 - 8401
Published: Nov. 20, 2023
We
presented
a
method
for
synthesizing
allylic
chiral
hydrazones
from
1,4-disubstituted
1,3-dienes
and
through
(R)-DTBM-Segphos-Pd(0)-catalyzed
hydrohydrazonation
reaction.
This
transformation
has
wide
range
of
substrates
good
functional
group
tolerance.
The
desired
products
were
obtained
in
medium
to
high
yield
regio-
enantioselectivity.
Synthetic
the
into
various
nitrogen-containing
compounds
was
demonstrated.
