Highly Enantioselective Organocatalytic Mannich Reaction of α-Benzylidene Succinimides with N-Boc Imines: Experimental and Theoretical Studies
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 24, 2025
The
development
of
efficient
and
practical
methods
for
the
construction
chiral
succinimide
frameworks,
which
are
backbone
various
natural
products
widely
studied
in
field
pharmaceuticals,
attracts
considerable
research
attention.
In
this
study,
an
asymmetric
Mannich
reaction
α-benzylidene
succinimides
with
N-Boc
imines
was
successfully
performed
using
a
bifunctional
squaramide-type
organocatalyst
derived
from
quinine,
affording
corresponding
adduct
two
contiguous
stereocenters
high
yields
(up
to
98%)
diastereoselectivities
>20:1
dr)
excellent
enantioselectivities
99%
ee).
This
protocol
provides
direct
approach
prepare
derivatives
simple
starting
material.
Density
Functional
Theory
(DFT)
calculations
conformational
search
autosampling
program
revealed
that
enantioselectivity
profile
dominated
by
deformation
organocatalyst.
Язык: Английский
Phosphine-Catalyzed [4 + 1] Annulation of β’-Acetoxy Allenoate with α-Alkylidene Succinimides: Access to Functionalized Spirosuccinimide Derivatives
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(22), С. 16711 - 16720
Опубликована: Окт. 31, 2024
A
phosphine-catalyzed
[4
+
1]
annulation
of
β'-acetoxy
allenoate
with
α-alkylidene
succinimides
is
described.
This
method
demonstrates
the
nucleophilic
dialkylation
and
cyclization
succinimides,
resulting
in
formation
functionalized
spirosuccinimide
derivatives.
The
reaction
exhibits
a
wide
substrate
scope
yields
ranging
from
moderate
to
excellent
under
optimized
conditions.
In
addition,
biological
evaluation
indicates
that
cycloadduct
3u
presents
satisfied
inhibitory
activities
for
three
human
cancer
cell
lines
(HCT116,
A549,
HepG2).
Язык: Английский
Base-Promoted Chemodivergent Construction of 2H-Chromen-2-one and Chromeno[2,3-c]pyrrole Scaffolds from para-Quinone Methides and α-Alkylidene Succinimides
Organic Letters,
Год журнала:
2024,
Номер
26(42), С. 9114 - 9119
Опубликована: Окт. 11, 2024
Herein,
we
evolve
a
base-promoted
synthesis
of
2
Язык: Английский
Diastereoselective Synthesis of Dearomatic 2‐oxa‐7‐azaspiro[4.5]decane Derivatives through Gold and Palladium Relay Catalytic Tandem Cyclization of Enynamides with Vinyl Benzoxazinanones
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(22), С. 4778 - 4785
Опубликована: Авг. 14, 2024
Abstract
We
present
a
diastereoselective
Au/Pd
relay
catalytic
tandem
cyclization
reaction
to
produce
dearomatic
2‐oxa‐7‐azaspiro[4.5]decane
derivatives
under
mild
conditions.
This
process
involves
generating
furan‐derived
azadiene
from
readily
available
enynamide,
followed
by
[2+4]
cycloaddition
with
Pd‐
π
‐allyl
dipole
decarboxylated
vinyl
benzoxazinanone.
Our
method
efficiently
constructs
the
spiro[4.5]decane
skeleton,
achieving
yields
ranging
31–97%
and
diastereoselectivities
6:1
dr
>20:1
across
34
examples.
research
introduces
new
sites
for
azadienes
as
1,2‐dipoles
offers
reliable
approach
constructing
oxa‐azaspiro[4.5]decane
frameworks.
Язык: Английский