Access to syn α‐Amino‐β‐Hydroxyesters by N‐H Insertion on O‐Protected α‐Diazo‐β‐Hydroxyesters.
Asian Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 13, 2024
Abstract
The
N−H
insertion
reaction
is
a
versatile
method
for
creating
C−N
bonds
under
mild
conditions,
providing
in
particular
an
efficient
access
to
both
natural
and
non‐natural
α‐amino
acid
derivatives.
In
this
field,
the
direct
on
α‐diazo‐β‐hydroxyesters
has
not
yet
been
investigated
constitutes
significant
challenge,
due
competitive
migration
processes.
We
report
herein
first
insertions
O
‐protected
α‐diazo‐β‐aryl‐β‐hydroxyesters,
enabling
synthesize
wide
range
of
α‐amino‐β‐hydroxyesters
by
tuning
nature
amine
aryl
substituent.
Overall,
28
products
have
isolated,
with
moderate
good
yields
most
cases,
diastereoisomeric
ratios
up
8.0
:
1
favor
syn
diastereoisomer.
Language: Английский
Synthesis of Functionalized Indoles by an Iridium-Catalyzed N–H Insertion Cascade: Nucleophilic Cyclization of Naphthylamines with α-Diazocarbonyl Compounds
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 28, 2024
A
novel
iridium-catalyzed
[3
+
2]
annulation
of
naphthylamines
and
α-diazocarbonyl
compounds
was
developed
for
the
rapid
assembly
densely
functionalized
indoles.
This
new
catalytic
process
represents
first
example
a
cascade
intramolecular
nucleophilic
cyclization
by
N-H
insertion
amines.
Various
could
be
obtained
in
high
yields
with
excellent
functional
group
tolerance.
The
reaction
affords
valuable
indole
derivatives,
enabling
expedient
access
to
heterocyclic
analogues
not
easily
accessible
other
methods.
Language: Английский