Synthesis of γ-Lactams via Palladium-Catalyzed C(sp3)–H Bond Activation of Alkyl Sulfonamides with Substituted Alkenes
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 20, 2025
A
methodology
for
the
γ-butyrolactam
scaffolds
via
ligand-enabled
C(sp3)–H
bond
functionalization
of
sulfonamides
with
olefins
has
been
demonstrated.
The
protocol
found
to
be
compatible
several
activated
and
unactivated
olefins,
desired
lactams
were
formed
in
excellent
yields.
plausible
mechanism
described
account
lactamization
reaction
as
well
supported
by
mechanistic
investigation
including
a
1H
NMR
study
isolation
palladacycle
intermediate.
Язык: Английский
Palladium-Catalyzed Directed Alkenylation of Alkyl Amides with Unactivated Alkenes: Access to γ-Alkenyl γ-Lactams
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 13, 2025
Pd(II)-catalyzed
cascade
C(sp3)–H
alkenylation
and
cyclization
of
alkyl
amides
with
readily
accessible
unactivated
alkenes
have
been
accomplished.
Alkenylation
subsequent
intramolecular
empowered
the
formation
functionalized
γ-lactams,
which
present
as
an
active
core
several
bioactive
natural
products.
The
use
catalytic
Cu(OAc)2
along
molecular
oxygen
oxidant,
a
2-chloropyridine
ligand,
site
selectivity,
substrate
scope,
gram-scale
synthesis
are
important
practical
features.
Язык: Английский
Synthesis of lactones and lactams via C(sp3)–H bond functionalization
Chemical Society Reviews,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
In
this
review,
we
have
showcased
the
diverse
aspects
of
transition-metal
catalysis,
biocatalysis,
and
photocatalytic
C(sp
3
)–H
bond
functionalization
to
access
lactones
lactams.
Язык: Английский
Enantioselective β-C(sp3)–H Nucleophilic Tosylation of Native Amides: A Synthetic Platform for Chiral Methyl Stereocenters
Journal of the American Chemical Society,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 31, 2025
Enantioselective
oxygenation
of
unactivated
C(sp3)-H
bonds
via
asymmetric
metalation
remains
an
unsolved
challenge.
Herein
we
report
the
development
a
Pd-catalyzed,
enantioselective
tosylation
native
amides
with
NaOTs
as
nucleophile,
representing
rare
example
C-H
functionalization
nucleophilic
coupling
partner.
High
enantioselectivity
in
this
reaction
is
achieved
by
chiral
monoprotected
amino
sulfonamide
(MPASA)
ligands.
Substantial
enhancement
silver
salt
additives
was
also
observed.
Through
desymmetrization
readily
available
isopropyl
moiety,
structurally
diverse
β-tosylated
bearing
α-methyl
stereocenter
were
obtained
high
yield
and
enantioselectivity,
which
complements
current
enzymatic
method
for
making
Roche
ester
synthon.
The
tosylated
products
are
highly
versatile
building
blocks
further
diversifications
nitrogen,
oxygen,
other
nucleophiles,
thus
providing
platform
constructing
methyl
stereocenters.
Язык: Английский