Asymmetric Aza-Michael/Michael/Mannich Domino Reaction of 2-Aminochalcones and 5-Alkenyl-Thiazolones: Access to Enantioenriched 1,4-Sulfur-Bridged Piperidinone Skeletons
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 15, 2025
Herein,
we
disclose
a
novel
organocatalytic
approach
for
the
enantioselective
synthesis
of
1,4-sulfur-bridged
piperidinone
skeletons
via
sequential
aza-Michael/Michael/Mannich
domino
reaction
2-aminochalcones
and
5-alkenyl-thiazolones.
The
one-pot
catalyzed
by
bifunctional
squaramide
catalyst
furnishes
bridged
polycyclic
compounds
with
five
contiguous
stereocenters
(three
tertiary,
two
heteroquaternary)
in
excellent
yields
(up
to
95%)
stereochemical
outcomes
99%
ee
up
>20:1
dr).
methodology
offers
outstanding
control
on
regio-
chemoselectivity,
showcasing
broad
substrate
compatibility.
Additionally,
is
scalable
postsynthetic
transformation
spirothiazolone-tetrahydroquinoline
derivative
further
amplifies
synthetic
utility
methodology.
Язык: Английский
Copper-catalyzed enantioselective propargylic [3 + 2] cycloaddition: access to oxygen heterocycles featuring a CF3-substituted quaternary stereocenter
Organic & Biomolecular Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
An
enantioselective
Cu(
i
)-catalyzed
propargylic
[3
+
2]
cycloaddition
reaction
for
the
synthesis
of
optically
active
oxygen
heterocycles
bearing
CF
3
-substituted
quaternary
stereocenters
has
been
realized.
Язык: Английский
Recent Advances in the Enantioselective Organocatalytic [4+2] Cycloadditions
Molecules,
Год журнала:
2025,
Номер
30(9), С. 1978 - 1978
Опубликована: Апрель 29, 2025
This
review
covers
the
recent
advances
in
asymmetric
organocatalytic
Diels–Alder
reactions
published
since
beginning
of
2015.
It
describes
approaches
to
enantioselective
[4+2]
cycloadditions
based
on
application
various
types
chiral
organocatalysts.
Язык: Английский
Enantioselective Synthesis of Spirooxindole‐pyran and furan Scaffolds via Copper‐Catalyzed Formal (3+3) and (3+2) Cycloaddition of Isatin‐derived Propargylic Esters
Chemistry - A European Journal,
Год журнала:
2024,
Номер
31(8)
Опубликована: Дек. 12, 2024
Herein,
we
report
a
copper-catalyzed
enantioselective
formal
(3+3)
and
(3+2)
cycloaddition
reaction
of
isatin-derived
tertiary
propargylic
esters
with
N,N-dimethylbarbituric
acid
4-hydroxycoumarins,
respectively.
In
this
process,
the
ester
serves
as
both
C3-
C2-synthons,
facilitating
synthesis
optically
active
spirooxindole-pyran
furan
scaffolds
featuring
an
all-carbon
quaternary
stereocenter.
The
delivers
these
spirocyclic
frameworks
in
good
yields
high
enantioselectivities.
Additionally,
scalability
reactions
transformation
chiral
intermediates
into
valuable
structures
emphasize
synthetic
practical
importance
strategy.
Язык: Английский