Synthesis of gem-Diborylcyclopropyl Ketones via Conjugate Addition of Chlorodiborylmethane to α,β-Unsaturated Ketones
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 3, 2025
The
carbanion
derived
from
chlorodiborylmethane
can
act
as
a
soft
nucleophile,
while
the
halogen
substituent
subsequently
function
leaving
group.
Taking
advantage
of
this
feature,
we
herein
have
developed
an
efficient
synthesis
gem-diborylcyclopropyl
ketones
diverse
range
enone
substrates.
We
also
demonstrated
synthetic
utility
protocol
by
leveraging
highly
transformable
nature
cyclopropyl
moiety
and
C-B
bonds.
Язык: Английский
Diastereoselective Synthesis of Boryl-Substituted Vinylcyclopropanes via Deborylative Cyclization of Geminal Diboron Compounds
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 14, 2025
Herein
we
report
a
diastereoselective
synthesis
of
boryl-substituted
vinylcyclopropanes,
class
highly
valuable
synthetic
building
blocks,
via
deborylative
cyclization
geminal
diboron
compounds.
The
method
exhibits
broad
functional
group
tolerance
and
accommodates
diverse
alkyl
aryl
α-substituents.
diastereoselectivity
is
primarily
governed
by
the
α-substituent
(alkyl
vs
aryl),
while
olefin
geometry
in
side
chain
has
secondary
influence.
Mechanistic
studies
indicated
distinct
pathways:
concerted
process
for
substrates
carbanion
intermediate
derivatives.
Synthetic
utility
products
was
also
demonstrated.
Язык: Английский