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6
(4 -6 mo l%)
air
RC H
2
NO
2
R
2
R
2
toluene
50-6 0 ºC
OH
O
d
n
4
r
4
n
g
|
1
R
1
R
1
NO
2
R
R
2
R
2
O
O
R
1
NO
2
NO
2
R
2
= Me, 93%, 90% ee
R
2
= A llyl, 92%, 90% ee
R
2
= Ph, 82%, 9 3% ee
R
2
=CCPh,91%,89%ee
R
1
= Et, 87%, 88% ee, R
2
=Me
R
1
=
-Hex, 75% , 89% ee , R
2
=Me
n
R
1
=
-Hex, 43 %, 96% ee , R
2
c
=Cl
R
2
= 3,5 -Cl
2
C
6
H
3
, 81% , 96% ee (
S
)
R
2
= Cl, 83%, 9 4% ee
R
2
= Br , 84%, 95% ee
R
2
= I, 8 7%, 8 8% ee
O
NO
2
R
R = Me , 86%, 96% ee, d r = 9/1
R = Et, 79%, 94% ee, dr = 10/1
Scheme 9.22
Iron-catalyzed asymmetric aerobic dearomatization of naphthols with
nitroalkanes.
.
O
2
O-O
O
O
LFe
III
R
LFe
III
R
7
8
O
CH
3
N
O
2
O
2
N
O-O
H
2
O
2
OOH
HO
HOO
R
O
O
LFe
III
R
R
NO
2
LFe
III
O
N
OOH
OOH
O
Scheme 9.23 Proposed mechanism of iron-catalyzed oxidative dearomatization of
2-naphthols.
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