Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(3), P. 488 - 493
Published: Jan. 13, 2023
Synthesis
of
chiral
phosphorus
compounds
from
readily
available
substrates
by
a
facile
method
is
an
attractive
strategy.
In
this
study,
efficient
route
for
copper-catalyzed
asymmetric
boroprotonation
phosphinylallenes
with
bis(pinacolato)diboron
high
regioselectivity
was
developed,
affording
allylphosphine
oxides
in
yields
enantioselectivities
up
to
98%
ee.
The
synthetic
utility
further
demonstrated
the
transformation
several
stereospecific
products.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(9), P. 3606 - 3614
Published: Jan. 1, 2023
We
describe
a
cobalta-electro-catalyzed
enantioselective
C–H
annulation
of
arylphosphinamides
with
alkynes
for
P-stereogenic
compounds
via
desymmetrization
and
kinetic
resolution
processes.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(15)
Published: Feb. 14, 2023
Abstract
A
general
and
mild
nickel‐catalyzed
enantioselective
C(sp
2
)−P
cross‐coupling
for
synthesizing
P‐stereogenic
phosphine
oxides
has
been
developed.
The
asymmetric
alkenylation/arylation
of
racemic
secondary
with
alkenyl/aryl
bromides
generated
high
yields
enantioselectivities.
Various
functional
groups
were
tolerated,
the
applications
this
method
demonstrated
through
late‐stage
functionalization
product
transformations.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(25)
Published: April 14, 2023
Abstract
Transition‐metal‐catalyzed
enantioselective
P−C
cross‐coupling
of
secondary
phosphine
oxides
(SPOs)
is
an
attractive
method
for
synthesizing
P
‐stereogenic
phosphorus
compounds,
but
the
development
such
a
dynamic
kinetic
asymmetric
process
remains
considerable
challenge.
Here
we
report
unprecedented
highly
intermolecular
coupling
SPOs
and
aryl
iodides
catalyzed
by
copper
complexes
ligated
finely
modified
chiral
1,2‐diamine
ligand.
The
reaction
tolerates
wide
range
iodides,
affording
tertiary
(TPOs)
in
high
yields
with
good
enantioselectivity
(average
89.2
%
ee).
resulting
enantioenriched
TPOs
were
transformed
into
structurally
diverse
‐chiral
scaffolds,
which
are
valuable
as
ligands
catalysts
synthesis.
ACS Catalysis,
Journal Year:
2023,
Volume and Issue:
13(20), P. 13301 - 13309
Published: Oct. 2, 2023
The
construction
of
phosphorus
stereocenters
under
metal-free
conditions
remains
a
formidable
challenge.
Herein,
we
report
mechanistically
distinct
chiral
electrophilic
selenium
catalysis-enabled
desymmetrizing
cyclization
to
access
valuable
phosphorus-stereogenic
heterocycles
with
high
efficiency.
This
ambient
temperature
method
affords
broad
range
compounds
that
bear
phenolic
hydroxyl
group
as
useful
synthetic
handle
and,
thus,
enriches
the
toolbox
for
rapid
generation
molecular
complexity.
control
experiments
and
DFT
calculations
indicate
dual-hydrogen-bonding
bridge
formed
between
substrate
TfO–
anion
plays
crucial
role
in
determining
enantioselectivity
transformation.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(13), P. 2178 - 2183
Published: Feb. 10, 2023
Copper-catalyzed
dynamic
kinetic
resolution
of
secondary
phosphine
oxides
has
been
successfully
developed,
providing
a
general
method
for
the
gram-scale
enantioselective
synthesis
P-stereogenic
cyclic
with
high
yields
and
enantioselectivities.
The
products
could
be
easily
reduced
to
corresponding
useful
P(III)-stereogenic
phosphines.
A
mechanism
involving
unusual
rapid
racemization
SPOs
proposed.
Journal of the American Chemical Society,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 19, 2025
Chiral
phosphoramidates
characterized
by
at
least
a
P–N
bond
without
P–C
demonstrate
significant
applicative
value
within
nucleoside
phosphoramidate
prodrugs.
Despite
the
availability
of
methodologies
for
selective
construction
diverse
chiral
organophosphorus
entities,
achieving
P-stereocenters
solely
substituted
heteroatoms
often
relies
on
diastereomeric
synthesis.
Here,
we
present
catalytic
enantioselective
desymmetrization
strategy
using
an
electrophilic
phosphorus
reagent
with
three
leaving
groups
as
substrate,
enabling
three-phase
nucleophilic
attack
various
alcohols
and
amines.
By
generating
broad
range
possible
substituent
combinations
around
atoms,
this
synthetic
may
expedite
synthesis
screening
biologically
active
phosphoramidates.
Chemical Science,
Journal Year:
2023,
Volume and Issue:
14(5), P. 1286 - 1290
Published: Jan. 1, 2023
Due
to
the
high
reactivity
of
triple
bond,
P-stereogenic
alkynylphosphines
could
be
easily
derivatized,
serving
as
universal
building
blocks
for
structurally
diverse
phosphine
compounds.
However,
synthesis
via
direct
P-C
bond
formation
was
unprecedented.
Here,
we
report
an
efficient
method
with
enantioselectivity
a
Ni-catalyzed
asymmetric
cross-coupling
reaction.
The
reaction
tolerate
variety
functional
groups,
affording
products
that
can
converted
into
useful
derivatives.
