Journal of the American Chemical Society,
Journal Year:
2023,
Volume and Issue:
145(48), P. 26504 - 26515
Published: Nov. 27, 2023
Conjugated
trienes
are
fascinating
building
blocks
for
the
rapid
construction
of
complex
polycyclic
compounds.
However,
limited
success
has
been
achieved
due
to
challenging
regioselectivity
control.
Herein,
we
report
an
enantio-
and
diastereoselective
process
allowing
regioselectively
control
functionalization
NH-triene-carbamates.
Synthesis
chiral
cis-3,6-dihydro-2H-1,2-oxazines
is
by
a
phosphoric
acid
catalyzed
Nitroso-Diels-Alder
cycloaddition
involving
[(1E,3E,5E)-hexa-1,3,5-trien-1-yl]carbamates.
Moreover,
modular
access
three
different
regioisomers
with
excellent
diastereoselectivities
high
enantioselectivities
obtained
careful
choice
reaction
conditions.
A
computational
study
reveals
that
influenced
steric
demand
substituents
at
6-position
triene,
as
well
noncovalent
interactions
between
two
partners.
Utility
each
regioisomeric
cycloadduct
highlighted
variety
synthetic
transformations.
RSC Advances,
Journal Year:
2023,
Volume and Issue:
13(7), P. 4843 - 4858
Published: Jan. 1, 2023
In
this
research
a
highly
efficient
and
heterogeneous
catalyst
of
ZSM-5@APTMS@(
E
)-4-((pyridin-2-ylimino)methyl)benzaldehyde@Cu-NPs
was
synthesized
for
upgrading
the
A
3
coupling
reaction
synthesis
propargylamines
under
mild
conditions.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(62), P. 9481 - 9484
Published: Jan. 1, 2023
A
catalyst-free
1,2-difunctionalization
of
1,3-dienes
with
CHCl3
and
TBHP
in
the
presence
NEt3
to
give
dichloromethylhydroxylation
products
was
developed.
Various
substituents
on
aryl
ring
dienes
tolerated
reactions
gave
corresponding
moderate
good
yields.
When
Na2CO3
employed
as
base,
key
intermediate
α-amino
radical
could
not
be
formed;
therefore,
1,2-peroxyhydroxylation
were
obtained
instead.
This
protocol
provides
an
effective
functional
group
tolerant
strategy
for
diene
1,2-difunctionalization,
thus
providing
great
potential
further
functionalization
modification
synthetic
molecules.
