Biomedical Engineering Reference
In-Depth Information
MesN
NMes
Cl
Cl
Ru
PCy
3
Ph
O
O
151
(1 mol%)
H
Me
H
+
Me
Me
CH
2
Cl
2
, EtOAc
40°C
O
O
150
69
152
Me
O
N
Me
H
Me
153
(20 mol%)
Ph
Me
O
TMSO
Me
154
-50°C
O
O
CO
2
H
Me
H
TESO
O
H
Me
O
O
Me
2
(30 mol%)
Me
H
Me
OH
rt
64%
Me
H
H
O
OTES
O
H
O
O
H
H
157
156
(ee = 95%, dr = 5:1)
155
Me
HO
H
Me
TESO
H
Me
H
OH
Me
H
OTES
Me
Me
Aromadendranediol (
159
)
158
SCHEME 6.31
Total synthesis of aromadendranediol via organocatalytic cascade
reaction.
corresponding terminal diene and diastereoselective cyclopropanation eventually
afforded aromadendranediol (
159
).
6.5. CONCLUSION
The examples presented in this chapter do not represent an exhaustive overview of the
field of enantioselective organocatalysis but tend to demonstrate how important this
area is for the synthetic organic chemist. With the readily available proline- and
imidazolidinone-derived organocatalysts and the successful applications in the
syntheses of complex bioactives, enantioselective organocatalysis has definitely
become a powerful tool.
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