Chemistry Reference
In-Depth Information
Table 16.6
Enantioselective addition of ketones to nitrodienes and nitro-eneyne.
11e
(15 mol%)
PhCO
2
H (5 mol%)
O
2
N
O
O
NO
2
+
Ar
1
Ar
2
Ar
1
Ar
2
CH
2
Cl
2
, rt, 6 days
Ar
1
Ar
2
Yield (%)
ee (%)
Ph
Ph
78
97
S
OPiv
Ph
4-MeOC
6
H
4
77
97
O
PivO
PivO
N
N
Ph
4-MeC
6
H
4
90
96
NH
2
OPiv
Ph
4-BrC
6
H
4
80
96
H
11e
H
Ph
4-ClC
6
H
4
72
94
Ph
4-FC
6
H
4
83
96
Ph
2-Naphthyl
70
97
Ph
3,4-OCH
2
OC
6
H
4
89
98
Ph
3-Py
79
94
Ph
2-Py
90
84
Ph
2-Furyl
58
95
Ph
2-Thienyl
56
85
2-NO
2
C
6
H
4
Ph
94
96
4-MeOC
6
H
4
Ph
48
99
O
2
N
O
O
11f
(15 mol%)
NO
2
+
PhCO
2
H (5 mol%)
Ar
1
Ar
1
*
H
2
O (2.0 equiv)
toluene, rt
()
n
()
n
Ar
1
Ketone
Yield
(%)
syn
/
anti
ee (%)
(
syn)
Ph
Cyclohexanone
94
70/30
95
OAc
Ph
Cyclopentanone
97
63/37
97
S
O
Ph
Dihydro-2
H
-
pyran-4(3
H
)-one
98
50/50
99
AcO
AcO
N
N
NH
2
OAc
H
11f
H
Ph
Dihydro-2
H
-
thiopyran-
4(3
H
)-one
92
55/45
88
Ph
Acetone
75
—
95
Ph
4-Methylpentan-
2-one
44
—
93
2-NO
2
C
6
H
4
Cyclohexanone
85
99/1
96
2-NO
2
C
6
H
4
Acetone
78
—
84
4-MeOC
6
H
4
Cyclohexanone
98
66/34
91
4-MeOC
6
H
4
Acetone
70
—
91
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