Asymmetric Cycloaddition of N-2,2,2-Trifluoroethylisatin Ketimines and Unsymmetrical Dicarbonyl-Activated Alkenes: Construction of 5′-Trifluoromethylated 3,2′-Pyrrolidinyl Spirooxindoles with Three Carbonyl Groups
Jin-Zhi He,
Bao-Lei Zhu,
Zhen-Hui Huang
и другие.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(18), С. 12924 - 12934
Опубликована: Авг. 28, 2024
The
asymmetric
cycloaddition
between
Язык: Английский
Synthesis of functionalized spiro[indanone-benzazepine] scaffolds via [4 + 3] annulation reaction of N-(o-chloromethyl)aryl amides with ninhydrin-derived Morita−Baylis−Hillman carbonates
Tetrahedron,
Год журнала:
2023,
Номер
150, С. 133772 - 133772
Опубликована: Дек. 1, 2023
Язык: Английский
Synthesis of Highly Functionalized Spirocycles and Pentafulvene‐Containing Dyes Involving 2‐(2′‐ketoalkyl)‐1,3‐indandiones
Chemistry - A European Journal,
Год журнала:
2023,
Номер
29(71)
Опубликована: Окт. 11, 2023
Synthesis
of
highly
functionalized
spiro[4.4]nonane
and
spiro[4.5]decane
motifs
by
the
reaction
dimethylacetylenedicarboxylate
(DMAD)
with
2-(2'-ketoalkyl)-1,3-indandiones
2-(3'-ketoalkyl)-1,3-indandiones,
respectively,
has
been
developed
utilizing
a
catalytic
amount
DABCO.
The
tertiary
hydroxy-containing
products
were
converted
into
fully
conjugated
pentafulvene
π-systems
in
an
acidic
medium
through
dehydration
unprecedented
C-C
bond
rearrangement.
Язык: Английский
Organocatalyzed Asymmetric Cascade Michael/Michael Reaction of α‐Alkylidene Succinimides with a 2‐(Trifluoromethylmethylene)indane‐1,3‐dione
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(41)
Опубликована: Июль 9, 2024
Abstract
A
diaminomethylenemalononitrile
organocatalyst
efficiently
promoted
asymmetric
cascade
Michael/Michael
reactions
between
a
2‐(trifluoromethylmethylene)indane‐1,3‐dione
derivative
and
α‐alkylidene
succinimides,
resulting
in
spiroindane‐1,3‐dione
derivatives.
These
derivatives
feature
four
consecutive
carbon
stereocenters,
including
one
stereocenter
with
trifluoromethyl
substituent,
were
formed
high
yield
excellent
enantioselectivity
(up
to
94
%
ee).
This
study
marks
the
first
successful
example
of
using
methyleneindane‐1,3‐dione
derivatives,
bearing
alkoxycarbonyl
groups
at
β‐position,
as
Michael
acceptors.
Язык: Английский
Organocatalyzed Enantioselective [3+2] Cycloaddition Reactions for Synthesis of Dispiro[benzothiophenone-indandione-pyrrolidine] Derivatives
Molecules,
Год журнала:
2024,
Номер
29(20), С. 4856 - 4856
Опубликована: Окт. 13, 2024
An
organocatalytic
enantioselective
[3+2]
cycloaddition
reaction
involving
2-arylidene-1,3-indandiones
and
Язык: Английский