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O
O
Ar
1
+
Ar
1
H
2
O/Dioxane
Ar
2
Ar
2
endo
/
exo
up to 98:2
ee up to 90% (
exo
)
FIGURE 16.11
Asymmetric Diels-Alder
reaction between cyclopentadiene and aza-
chalcones catalyzed by a DNA-based catalyst.
O
R
N
CO
2
Me
*
Michael additions
CO
2
Me
ee up to 99%
O
R
O
OH
N
NO
2
N
R
*
*
CO
2
Me
ee up to 94%
CO
2
Me
ee up to 83%
syn
-Hydration
CH
3
NO
2
H
2
O
O
N
R
Diels-Alder
H
N
O
R
O
R
N
N
*
NH
O
R
ee up to 93%
ee up to 83%
N
N
*
Friedel-Crafts
ee up to 81%
FIGURE 16.12
Examples of DNA-based asymmetric catalysis.
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