Inherently Chiral Seven- and Eight-Membered Rings: Enantioselective Synthesis and Applications
Yu Luo,
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Shuang Luo,
No information about this author
Qiang Zhu
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et al.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 17, 2025
Compared
to
smaller
or
larger
rings,
seven-
and
eight-membered
carbo-
heterocycles
are
typically
nonplanar
exhibit
greater
conformational
rigidity.
This
property
alone
can
impart
chirality
certain
7-
8-membered
ring
systems.
Herein,
we
summarize
recent
achievements
in
the
enantioselective
synthesis
of
this
class
inherently
chiral
medium
including
both
construction
modification,
as
well
applications
ligands
catalysts
derived
from
these
rigid
cyclic
scaffolds
asymmetric
catalysis.
Language: Английский
Catalytic Enantioselective Chlorofunctionalizations of N-Substituted Amides Using In Situ Generated HOCl as Hydrogen Bond Source
Tengbo Ding,
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Long Liang,
No information about this author
Moucun Yuan
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et al.
Journal of the American Chemical Society,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 29, 2025
Asymmetric
organocatalytic
halocyclization
represents
a
powerful
method
for
the
synthesis
of
valuable
chiral
haloheterocycles.
However,
its
heavy
dependence
on
substrates
that
contain
hydrogen
bond
donors
enantiocontrol
limits
broader
application.
Here
we
report
catalytic
asymmetric
chlorofunctionalization
olefinic
amides
do
not
bear
donors,
allowing
efficient
production
chlorooxazolidin-2-ones
and
chloroamino
esters
featuring
quaternary
stereocenters,
achieved
with
high
yields
excellent
enantioselectivity.
This
protocol
facilitates
N-aryloxazolidin-2-ones
establishes
useful
framework
synthesizing
antibiotic
analogues.
Mechanistic
studies
indicate
trace
amounts
water
interact
chlorinating
agent
to
produce
HOCl
in
situ,
which
acts
as
both
proton
donor
hypochlorite
source,
thereby
promoting
cyclization
process.
strategy
significantly
broadens
potential
development
diverse
array
functional
molecules.
Language: Английский