Enantioselective Tsuji‐Trost α‐Fluoroallylation of Amino Acid Esters with Gem‐Difluorinated Cyclopropanes
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(23)
Опубликована: Фев. 27, 2024
A
novel
enantioselective
Tsuji-Trost-type
cross
coupling
reaction
between
gem-difluorinated
cyclopropanes
and
N-unprotected
amino
acid
esters
enabled
by
synergistic
Pd/Ni/chiral
aldehyde
catalysis
is
presented
herein.
This
transformation
streamlined
the
diversity-oriented
synthesis
(DOS)
of
optically
active
α-quaternary
α-amino
bearing
a
linear
2-fluoroallylic
motif,
which
served
as
an
appealing
platform
for
construction
other
valuable
enantioenriched
compounds.
The
key
intermediates
were
confirmed
HRMS
detection,
while
DFT
calculations
revealed
that
excellent
enantioselectivity
was
attributed
to
stabilizing
non-covalent
interactions
Pd(II)-π-fluoroallyl
species
Ni(II)-Schiff
base
complex.
Язык: Английский
Palladium/Amine Dual-Catalyzed Tsuji–Trost Fluoroallylation of Aldehydes with gem-Difluorinated Cyclopropanes
Organic Letters,
Год журнала:
2024,
Номер
26(25), С. 5375 - 5379
Опубликована: Июнь 12, 2024
We
herein
disclose
the
Pd/amine
dual-catalyzed
ring-opening
cross-coupling
reaction
between
Язык: Английский
Synergistic Pd/Ni Dual-Catalyzed Cross-Coupling of Azaaryl Acetates with gem-Difluorinated Cyclopropanes
Organic Letters,
Год журнала:
2024,
Номер
26(41), С. 8956 - 8960
Опубликована: Окт. 7, 2024
We
herein
report
the
development
of
a
novel
Pd/Ni
dual-catalyzed
ring-opening
functionalization
Язык: Английский
Ruthenium-catalyzed C–H functionalization of indoles and indolines with 7-azabenzonorbornadienes: access to aminodihydronaphthyl indoles and indolines
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(25), С. 5159 - 5169
Опубликована: Янв. 1, 2024
An
Ru-catalyzed
carbamoyl-directed
C–H
functionalization
of
indoles
and
indolines
with
7-azabenzonorbornadienes
results
in
2-aminodihydronaphthyl
7-aminodihydronaphthyl
indolines,
respectively.
Язык: Английский
Electrocatalytic Enantioselective Tandem C–H Indolization toward Biindolyl Atropisomers: Reaction Development and Mechanistic Insight
ACS Catalysis,
Год журнала:
2025,
Номер
15(3), С. 1422 - 1430
Опубликована: Янв. 9, 2025
The
electrochemical
methods
for
asymmetric
indolization
are
still
elusive
and
pose
a
significant
challenge.
Taking
advantage
of
2-alkynylanilines
as
electrochemically
compatible
indolyl
equivalents,
we
herein
represent
mild
highly
enantioselective
electrocatalytic
process
tandem
C–H
to
form
2,3′-biindolyl
atropisomers
along
with
hydrogen
evolution
reaction.
Integrated
experimental
computational
mechanistic
studies
revealed
that
sequential
metalation/nucleophilic
cyclization/reductive
elimination/anodic
oxidation
sequence
involving
RhIII–RhI–RhIII
catalytic
cycle
accounts
the
established
transformation.
Язык: Английский
Palladium-Catalyzed Dearomative Fluoroallylation of Pyrroles with gem-Difluorinated Cyclopropanes
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 26, 2025
We
herein
report
the
development
of
a
novel
Pd-catalyzed
dearomative
functionalization
pyrroles
with
gem-difluorinated
cyclopropanes
(gem-F2CPs).
This
dearomative/ring-opening
strategy
streamlines
diversity-oriented
synthesis
(DOS)
α-quaternary
2-fluoroallylic
2H-pyrroles
broad
scope
and
excellent
functional
group
tolerance,
which
enables
efficient
late-stage
transformation
complex
bioactive
molecule-derived
gem-F2CPs.
Derivation
resulting
fluoroallylic
to
different
synthetically
useful
2H-pyrrole
motifs
demonstrated
synthetic
value
this
methodology.
Язык: Английский
Mo-Mediated Reductive Cyclization/Allylation of 2-Alkynyl Nitroarenes with 1,3-Dienes: Synthesis of 3-Allylindoles
Jia-Yi Feng,
Jian-Bang Hu,
Yi Liu
и другие.
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 28, 2025
3-Allylindoles
constitute
a
key
structural
feature
in
many
natural
products
and
bioactive
compounds.
In
this
work,
we
developed
Mo-mediated
reductive
cyclization/allylation
of
2-alkynyl
nitroarenes
with
1,3-dienes.
Using
Mo(CO)6
as
both
the
reductant
catalyst,
broad
range
functionalized
3-allylindoles
were
prepared
good
to
excellent
yields
from
easily
available
2-alkynylnitroarenes
1,3-dienes
starting
materials.
Язык: Английский
Palladium(II)-Catalyzed Enantioselective Ring Opening of Oxabenzonorbornadienes via Domino Aminopalladation of Alkynylanilines
Organic Letters,
Год журнала:
2024,
Номер
27(1), С. 369 - 375
Опубликована: Дек. 30, 2024
We
report
herein
a
robust
enantioselective
ring
opening
coupling
of
oxabenzonorbornadienes
via
Pd(II)-catalyzed
domino
cyclization
alkynylanilines,
which
features
the
formation
three
covalent
bonds
and
two
contiguous
stereocenters
with
excellent
enantio-
diastereoselectivity
broad
substrate
scope.
The
good
functional
group
tolerance
this
desymmetrization
strategy
enables
efficient
late-stage
transformation
natural
product-derived
alkynylanilines.
resulting
indolated
dihydronaphthols
could
serve
as
valuable
platform
to
streamline
diversity-oriented
synthesis
other
enantioenriched
tetrahydronaphthalene
derivatives.
Язык: Английский
Enantioselective Tsuji‐Trost α‐Fluoroallylation of Amino Acid Esters with Gem‐Difluorinated Cyclopropanes
Angewandte Chemie,
Год журнала:
2024,
Номер
136(23)
Опубликована: Фев. 27, 2024
Abstract
A
novel
enantioselective
Tsuji–Trost‐type
cross
coupling
reaction
between
gem
‐difluorinated
cyclopropanes
and
N
‐unprotected
amino
acid
esters
enabled
by
synergistic
Pd/Ni/chiral
aldehyde
catalysis
is
presented
herein.
This
transformation
streamlined
the
diversity‐oriented
synthesis
(DOS)
of
optically
active
α‐quaternary
α‐amino
bearing
a
linear
2‐fluoroallylic
motif,
which
served
as
an
appealing
platform
for
construction
other
valuable
enantioenriched
compounds.
The
key
intermediates
were
confirmed
HRMS
detection,
while
DFT
calculations
revealed
that
excellent
enantioselectivity
was
attributed
to
stabilizing
non‐covalent
interactions
Pd(II)‐π‐fluoroallyl
species
Ni(II)‐Schiff
base
complex.
Язык: Английский