Site‐Selective Direct γ‐Difunctionalization of Diazoenals: Application to the Synthesis of Enal‐Functionalized Allenes and Furans
Chemistry - An Asian Journal,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 23, 2024
A
new
approach
for
the
synthetically
important
γ-functionalized
enals
has
been
developed.
The
strategy
involves
rhodium-catalyzed
direct
C-C
&
C-S
bond
forming
site-selective
γ-difunctionalization
of
diazoenals
with
aryl
propargyl
sulfides
via
sulfur
ylide
[2,3]
sigmatropic
rearrangement,
resulting
in
highly
functionalized
γ-allenyl(sulfanyl)enals
excellent
yield
at
ambient
temperature.
This
versatile
constitutes
a
viable
alternative
to
remote
carbonyl-directed
γ-functionalization
unmodified
which
suffer
from
competitive
side
reactions.
synthetic
utility
was
demonstrated
by
InCl
Язык: Английский
Copper-enalcarbenoids: Rapid access to 1,7-disubstituted indoles via [4+2] benzannulation between diazoenals and N-substituted pyrroles
Tetrahedron Letters,
Год журнала:
2024,
Номер
unknown, С. 155331 - 155331
Опубликована: Окт. 1, 2024
Язык: Английский
Synergistic Rh(II)- and Zn(II)-Catalyzed [3 + 3] Annulation of Diazoenals and α-Hydroxy Ketones for the Direct Synthesis of 2H-Pyrans, A Gateway Toward γ-Pyrones
Organic Letters,
Год журнала:
2024,
Номер
26(43), С. 9227 - 9232
Опубликована: Окт. 21, 2024
A
new
synergistic
Rh(II)/Zn(II)-catalyzed
[3
+
3]
annulation
has
been
developed
between
diazoenals
and
α-hydroxy
ketones
enabling
the
direct
synthesis
of
4-formyl-2H-pyrans.
The
reaction
involves
formation
protic
oxonium
ylides
from
highly
electrophilic
Rh-enalcarbenoids
followed
by
Zn-templated
regioselective
intramolecular
aldol
condensation.
Subsequent
investigations
demonstrated
that
4-formyl-2H-pyrans
are
unique
precursors
γ-pyrones.
γ-pyrones
were
obtained
via
Et3N-mediated
oxidative
deformylation.
Further,
triflic-acid-promoted
double
Schmidt
provides
synthetically
important
carboxamide-substituted
4-cyano
2H-pyrans.
Язык: Английский