Proline Analogues
Chemical Reviews,
Journal Year:
2024,
Volume and Issue:
124(13), P. 8130 - 8232
Published: June 28, 2024
Within
the
canonical
repertoire
of
amino
acid
involved
in
protein
biogenesis,
proline
plays
a
unique
role
as
an
presenting
modified
backbone
rather
than
side-chain.
Chemical
structures
that
mimic
but
introduce
changes
into
its
specific
molecular
features
are
defined
analogues.
This
review
article
summarizes
existing
chemical,
physicochemical,
and
biochemical
knowledge
about
this
peculiar
family
structures.
We
group
analogues
from
following
compounds:
substituted
prolines,
unsaturated
fused
structures,
ring
size
homologues,
heterocyclic,
e.g.,
pseudoproline,
bridged
proline-resembling
overview
(1)
occurrence
nature
their
chemical
synthesis,
(2)
physicochemical
properties
including
conformation
Language: Английский
Recent advances in organocatalytic atroposelective reactions
Henrich Szabados,
No information about this author
Radovan Šebesta
No information about this author
Beilstein Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
21, P. 55 - 121
Published: Jan. 9, 2025
Axial
chirality
is
present
in
a
variety
of
naturally
occurring
compounds,
and
becoming
increasingly
relevant
also
medicine.
Many
axially
chiral
compounds
are
important
as
catalysts
asymmetric
catalysis
or
have
chiroptical
properties.
This
review
overviews
recent
progress
the
synthesis
via
organocatalysis.
Atroposelective
organocatalytic
reactions
discussed
according
to
dominant
catalyst
activation
mode.
For
covalent
organocatalysis,
typical
enamine
iminium
modes
presented,
followed
by
N
-heterocyclic
carbene-catalyzed
reactions.
The
bulk
devoted
non-covalent
activation,
where
Brønsted
acids
feature
most
prolific
catalytic
structure.
last
part
article
discusses
hydrogen-bond-donating
other
motifs
such
phase-transfer
catalysts.
Language: Английский
Stereoselective Synthesis of Atropisomeric Amides Enabled by Intramolecular Acyl Transfer
Jack M. Wootton,
No information about this author
Natalie J. Roper,
No information about this author
C. Morris
No information about this author
et al.
Chemical Science,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
A
stereoselective
strategy
to
make
C–N
atropisomeric
amides
based
on
intramolecular
acyl
transfer
via
a
tethered
Lewis
basic
pyridine
or
tertiary
amine
group
is
reported.
Language: Английский
Guanidium Unmasked: Repurposing Common Amide Coupling Reagents for the Synthesis of Pentasubstituted Guanidine Bases
Juhana A. S. Aho,
No information about this author
Jere K. Mannisto,
No information about this author
S Mattila
No information about this author
et al.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 11, 2025
Guanidines
make
up
a
class
of
compounds
with
important
applications
in
catalysis
and
medicinal
chemistry.
In
this
systematic
study,
we
report
on
the
guanylation
aliphatic
amines,
anilines,
(sulfon)amides,
ureas,
carbamates
by
repurposing
HATU,
common
amide
coupling
reagent.
The
products
are
2-substituted
1,1,3,3-tetramethylguanidines
(TMGs),
group
sterically
hindered
superbases.
reaction
guanidinium
salt
amines
has
been
regarded
as
an
unwanted
side-reaction
coupling,
yet
exact
mechanistic
details
have
unclear.
Our
investigation
shows
that
is
highly
dependent
nature
nitrogen
nucleophile.
findings
were
applied
two
fronts:
minimizing
competing
reactions
well
maximizing
simple
one-step
synthesis
broad
variety
TMGs,
including
late-stage
functionalization
pharmaceuticals.
Language: Английский
Catalytic Enantioselective Sulfoxidation of Functionalized Thioethers Mediated by Aspartic Acid-Containing Peptides
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(32), P. 6872 - 6877
Published: Aug. 5, 2024
A
peptide-catalyzed
enantioselective
oxidation
of
sulfides
to
yield
pharmaceutically
relevant
chiral
sulfoxides
is
reported.
Experimental
evidence
suggesting
that
a
hydrogen
bond-donating
moiety
must
be
present
in
the
substrate
achieve
high
levels
enantioinduction
supported
by
computational
modeling
transition
states.
These
models
also
indicate
dual
points
contact
between
peptidic
catalyst
and
are
likely
responsible
for
formation
one
desired
sulfoxide
94:6
er.
Language: Английский