Dynamic Kinetic Asymmetric Hydroacylation: Racemization by Soft Enolization
Mengfei Xu,
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Stephanie A. Corio,
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Josephine M. Warnica
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et al.
Journal of the American Chemical Society,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 29, 2025
We
report
a
dynamic
kinetic
asymmetric
transformation
(DyKAT)
of
racemic
aldehydes
by
Rh-catalyzed
hydroacylation
acrylamides.
This
intermolecular
generates
1,4-ketoamides
with
high
enantio-
and
diastereoselectivity.
DFT
experimental
studies
provide
mechanistic
insights
reveal
an
unexpected
pathway
for
aldehyde
racemization.
Our
study
represents
pioneering
resolution
contributes
to
the
growing
field
stereoconvergent
catalysis
featuring
C-C
bond
construction.
Language: Английский
Rhodium-Catalyzed Asymmetric Hydrogenation and Transfer Hydrogenation of α-Nitro Ketones
Hao Sun,
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Liren Xu,
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Sai Ruan
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et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(46), P. 10008 - 10012
Published: Nov. 13, 2024
A
catalytic
protocol
for
the
enantioselective
hydrogenation
and
transfer
of
α-nitro
ketones
was
developed,
providing
a
wide
range
β-nitro-α-phenylethanols
with
high
yields
excellent
enantioselectivities
(up
to
98%
yield
up
>99.9%
ee).
Compatibility
solvents
bases
demonstrates
robustness
this
reaction.
The
synthetic
potential
demonstrated
by
TON
experiment
as
well
application
in
synthesis
key
intermediates
mirabegron
(S/C
=
10,000,
95%
yield,
99%
Language: Английский