Enantioselective Construction of Tetrahydroindole Skeletons by Rh‐Catalyzed [2+2+2] Cycloaddition of Homopropargyl Enamides with Alkynes
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(38)
Опубликована: Июнь 26, 2024
We
have
developed
the
Rh-catalyzed
enantioselective
[2+2+2]
cycloaddition
of
homopropargyl
enamides
(tosylamide-tethered
1,6-enynes)
with
alkynes
to
construct
tetrahydroindole
skeletons
found
in
natural
alkaloids
and
pharmaceuticals.
This
proceeds
at
room
temperature
high
yields
regio-
enantioselectivity
a
broad
substrate
scope.
The
preparative
scale
reaction
followed
by
substituent
conversion
on
nitrogen
atom
diastereoselective
[4+2]
singlet
O
Язык: Английский
Enantioselective Construction of Tetrahydroindole Skeletons by Rh‐Catalyzed [2+2+2] Cycloaddition of Homopropargyl Enamides with Alkynes
Angewandte Chemie,
Год журнала:
2024,
Номер
136(38)
Опубликована: Июнь 26, 2024
Abstract
We
have
developed
the
Rh‐catalyzed
enantioselective
[2+2+2]
cycloaddition
of
homopropargyl
enamides
(tosylamide‐tethered
1,6‐enynes)
with
alkynes
to
construct
tetrahydroindole
skeletons
found
in
natural
alkaloids
and
pharmaceuticals.
This
proceeds
at
room
temperature
high
yields
regio‐
enantioselectivity
a
broad
substrate
scope.
The
preparative
scale
reaction
followed
by
substituent
conversion
on
nitrogen
atom
diastereoselective
[4+2]
singlet
O
2
affords
hexahydroindole‐diols
bearing
three
stereogenic
centers
variable
substituents
nitrogen.
Mechanistic
studies
revealed
that
enynes
change
ratio
intramolecular
intermolecular
rhodacycle
formation
when
using
terminal
alkynes,
varying
ee
values
cycloadducts.
Язык: Английский