Enantioselective Catalytic Aldol Reactions in the Presence of Knoevenagel Nucleophiles: A Chemoselective Switch Optimized in Deep Eutectic Solvents Using Mechanochemistry
Hanaa Al Beiruty,
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Sofiia-Stefaniia Zhylinska,
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Nino Kutateladze
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et al.
Molecules,
Journal Year:
2023,
Volume and Issue:
29(1), P. 4 - 4
Published: Dec. 19, 2023
In
the
presence
of
different
nucleophilic
Knoevenagel
competitors,
cyclic
and
acyclic
ketones
have
been
shown
to
undergo
highly
chemoselective
aldol
reactions
with
aldehydes.
doing
so,
substrate
breadth
for
this
emerging
methodology
has
significantly
broadened.
The
method
is
also
no
longer
beholden
proline-based
catalyst
templates,
e.g.,
commercially
available
O-t-Bu-L-threonine
advantageous
ketones.
key
insight
was
exploit
water-based
mediums
under
conventional
(in-water)
non-conventional
(deep
eutectic
solvents)
conditions.
With
few
exceptions,
high
aldol-to-Knoevenagel
chemoselectivity
(>10:1)
good
product
profiles
(yield,
dr,
ee)
were
observed,
but
only
in
DESs
conjunction
ball
milling
did
short
reaction
times
occur.
Language: Английский
Construction of three contiguous stereocenters through amine-catalyzed asymmetric aldol reactions
Ryoga Hikawa,
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Mio Shimogaki,
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Taichi Kano
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et al.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(54), P. 8424 - 8427
Published: Jan. 1, 2023
Three
contiguous
stereocenters
were
constructed
by
an
amino
acid-catalyzed
asymmetric
aldol
reaction
of
α-siloxyketones
with
racemizable
α-haloaldehydes
via
dynamic
kinetic
resolution.
One-pot
catalytic
synthesis
the
highly
functionalized
products
could
also
be
accomplished
α-bromination
simple
aldehydes
and
subsequent
reaction.
Language: Английский