Diels Alder Stereochemistry

Diels Alder Stereochemistry -...

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Unformatted text preview: Diels
Alder
Reac-on
‐
Stereoselec-vity
 •  Which
stereoisomer
is
preferred
in
the
following
Diels‐Alder
reac-on?
 O O H O H or H How
to
draw
stereochemical
 configura-on
of
the
product
 1.  Draw
 both
 molecules
in
the
plane
of
the
 paper
 with
 the
 diene
 on
 top
 and
 the
 carbonyl
 group
 of
the
 dieneophile
 tucked
under
the
 diene
so
it
 can
be
close
to
the
developing
π‐bond.
 2.  Draw
in
all
the
H
atoms
on
the
C
atoms
that
are
 going
to
become
stereogenic
centers
 3.  Draw
 product
 where
 all
 subs-tuents
 to
 the
 right
in
the
previous
diagram
are
on
one
side
of
 the
 new
 molecule.
 That
 is,
 all
 highlighted
 H
 atoms
are
cis
to
each
other.
 4.  Draw
 final
 structure
 of
 the
 product
 with
 the
 stereochemistry
 of
 the
 other
 subs-tuents
 shown
 too.
 This
 is
 the
 endo
 product
 of
 this
 Diels‐Alder
reac-on.
 ...
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