Journal of the Brazilian Chemical Society,
Journal Year:
2022,
Volume and Issue:
unknown
Published: Sept. 28, 2022
Chiral
aminomethylnaphthols
have
been
prepared
highly
diastereoselective
by
means
of
three-component
“Betti
condensation”,
using
steroidal
2-naphthol
analogue,
synthesized
from
estrone.
The
use
2-methoxybenzaldehyde
or
2-pyridinecarboxaldehyde
as
aldehyde
component
and
(S)-(–)-1-phenylethan-1-amine
(S)-(–)-1-(naphthalen-2-yl)ethan-1-amine,
chiral
non-racemic
amine
providing
the
diastereoselectivity,
allowed
synthesis
structurally
diverse
aminomethylnaphthols.
latter
easily
form
1,3-dihydronaphthoxazines
through
reaction
with
formaldehyde.
absolute
configurations
new
determined
advanced
nuclear
magnetic
resonance
(NMR)
experiments
confirmed
X-ray
crystallography.
obtained
pure
diastereoisomers
evaluated
pre-catalysts
in
enantioselective
addition
diethylzinc
to
aldehydes
enantioselectivities
up
97%
ee.
Molbank,
Journal Year:
2022,
Volume and Issue:
2022(4), P. M1522 - M1522
Published: Dec. 8, 2022
The
Betti
reaction
of
2-naphthol,
benzaldehyde
and
(S)-1-(4-nitrophenyl)ethylamine
without
any
solvent
gave
the
corresponding
aminobenzylnaphthol,
that
is
(S,S)-1-(phenyl((1′-4-nitrophenyl-ethyl)amino)methyl)-2-naphthol,
in
good
yield
(56%).
absolute
configuration
title
compound
was
attributed
by
NMR
analysis,
a
procedure
reliable
if
compared
with
data
obtained
X-ray
diffraction
experiments.
Molbank,
Journal Year:
2023,
Volume and Issue:
2023(3), P. M1695 - M1695
Published: July 14, 2023
The
complex
structure
of
aminobenzylnaphthols
can
be
easily
obtained
with
the
useful
Betti
reaction.
These
valuable
compounds
give
rise
to
chiral
intermediates,
that
found
wide
application
in
asymmetric
synthesis.
1-[(1S)-(4-Fluorophenyl)-((1′S)-1′-naphthalen-1-yl-ethylamino)-methyl]-naphthalen-2-ol
1
was
treated
triflic
anhydride
yield
corresponding
(S,S)-triflate
2,
which
is
a
intermediate
future
synthesis
aminophosphine,
used
catalysis.
Preliminarily
structural
considerations
based
upon
H(1)-NMR
spectroscopy
are
also
reported.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(24), P. 17069 - 17087
Published: Nov. 28, 2023
Metal
ion
complexes
frequently
show
substituted
1,4,7-triazacyclononane
(tacn)
as
the
ligand.
Besides
providing
donor
atoms
for
complex
formation,
tacn
serves
a
scaffold
equipping
with
further
functional
units
that
are
needed
complementation
and
electronic
tuning
of
metal
coordination
sphere
and/or
add
other
features,
e.g.,
light-absorbing
antennas
groups
bioconjugation.
To
exploit
full
potential
tacn,
strategies
directed
syntheses
NO(R1,R1,R2)
NO(R1,R2,R3),
i.e.,
two
even
three
different
substituents
R,
needed.
Herein,
we
report
strategy
takes
advantage
solid-phase
synthesis
in
assembly
precursors
NO(R1,R1,H)
NO(R1,R2,H).
The
NO(R1,R2,H)
is
based
on
highly
selective
formation
NO(Cbz,tfAc,H),
Cbz
being
link
between
solid
phase.
For
this,
was
loaded
onto
(4-nitrophenyl
carbonate)-resin,
thereby
forming
resin-bound
(rb)-tacn,
which
corresponds
to
NO(Cbz,H,H)
bound
Treatment
rb-tacn
ethyl
trifluoroacetate
gave
rb-NO(tfAc,H),
NO(Cbz,tfAc,H).
With
rb-NO(tfAc,H)
hand,
variety
were
prepared,
showing
broad
applicability
respect
type
reactions
(nucleophilic
substitution,
reductive
amination,
aza-Michael
addition,
addition
epoxides,
acylation).
study
also
identified
limitations
points
improvement.
Synlett,
Journal Year:
2024,
Volume and Issue:
unknown
Published: May 6, 2024
Abstract
A
catalyst-
and
solvent-free
procedure
has
been
developed
for
the
synthesis
of
p-[(
benzothiazolylamino)(aryl/heteroaryl)methyl]-functionalized
phenols
its
O-tosylates
via
one-pot
three-component
coupling
reaction
thymol
or
carvacrol,
aryl/heteroaryl
aldehydes,
2-aminobenzothiazoles
with
high
selectivity.
The
present
amino
methylation
process
is
convenient
to
perform
even
on
large
scale
a
broad
scope.
products
were
likely
formed
through
initial
para
attack
aldehydes
generate
p-quinone
methide
intermediate
subsequent
1,6-aza-Michael
addition
in-situ
generated
intermediate.
Molbank,
Journal Year:
2022,
Volume and Issue:
2022(4), P. M1528 - M1528
Published: Dec. 15, 2022
The
solvent-free
Betti
reaction
of
2-naphthol,
4-nitrobenzaldehyde
and
(S)-valine
methyl
ester
gave
the
corresponding
aminobenzylnaphthol
(S,S)-2-(((hydroxynaphth-1-yl)(4′-nitrophenyl)methyl)amino)-3-methylbutanoic
acid
in
good
yield
(59%).
This
product
was
fully
characterized.
We
observed
that
racemization
occurs
some
reactions
with
absent
this
reaction,
thus
predominant
(S,S)-product
obtained.
Molecules,
Journal Year:
2023,
Volume and Issue:
28(23), P. 7835 - 7835
Published: Nov. 29, 2023
Bifunctional
thioureas
and,
for
the
first
time,
bifunctional
thiosquaramides
as
organocatalysts
were
used
in
asymmetric
Betti
reaction
involving
1-,
2-naphthols
and
hydroxyquinoline
with
N-tosylimine
ketimine.
The
described
methodology
affords
direct
access
to
chiral
aminoarylnaphthols
excellent
yield
(up
98%)
high
enantioselectivity
80%
ee)
enantioenriched
3-amino-2-oxindoles
78%
yield,
up
98%
ee).
Journal of the Brazilian Chemical Society,
Journal Year:
2022,
Volume and Issue:
unknown
Published: Sept. 28, 2022
Chiral
aminomethylnaphthols
have
been
prepared
highly
diastereoselective
by
means
of
three-component
“Betti
condensation”,
using
steroidal
2-naphthol
analogue,
synthesized
from
estrone.
The
use
2-methoxybenzaldehyde
or
2-pyridinecarboxaldehyde
as
aldehyde
component
and
(S)-(–)-1-phenylethan-1-amine
(S)-(–)-1-(naphthalen-2-yl)ethan-1-amine,
chiral
non-racemic
amine
providing
the
diastereoselectivity,
allowed
synthesis
structurally
diverse
aminomethylnaphthols.
latter
easily
form
1,3-dihydronaphthoxazines
through
reaction
with
formaldehyde.
absolute
configurations
new
determined
advanced
nuclear
magnetic
resonance
(NMR)
experiments
confirmed
X-ray
crystallography.
obtained
pure
diastereoisomers
evaluated
pre-catalysts
in
enantioselective
addition
diethylzinc
to
aldehydes
enantioselectivities
up
97%
ee.
