Chemistry Reference
In-Depth Information
ArB(OH)
2
B(OH)
3
Rh
I
L
n
Cl
KOH
O
O
R
2
O
OH
R
1
Rh
I
LnAr
Rh
I
L
n
OH
R
1
R
2
Ar
68
69
H
2
O
H
O
ORh
I
Ln
Ar
R
1
Rh
I
Ln
O
H
R
1
R
2
Ar
R
2
R
1
R
2
O
O
R
1
R
2
Ar
O
O
O
Rh
I
Ln
71
Ar
Rh
I
Ln
70
Scheme 8C.29.
O
R
1
O
[Rh(COD)(OMe)]
2
(2.5 mol %)
(
S
)-BINAP (7.5 mol %)
OH
R
2
O
R
2
R
1
Ar
R
3
R
3
ArB(OH)
2
(200 mol %)
KOH (10 mol %), H
2
O (500 mol %)
Dioxane (0.1 M), 95°C
n
n
Me
Me
O
O
73
72
>99:1 de; 85->99% ee
n
= 1, 2
R
1
R
2
R
3
Entry
n
Ar
Yield (%)
% ee
1
CH
3
-(CH
2
)
2
-
1
p
-MeO-Ph
83
90
2
CH
3
-(CH
2
)
2
-
1
Ph
87
90
Ph
-(CH
2
)
2
-
1
Ph
94
87
3
4
CH
3
-(CH
2
)
2
-
1
p
-Br-Ph
88
94
5
CH
3
-(CH
2
)
3
-
1
p
-MeO-Ph
97
90
6
CH
3
-(CH
2
)
3
-
1
Ph
87
91
Ph
7
-(CH
2
)
3
-
1
Ph
86
85
8
CH
3
-(CH
2
)
3
-
1
p
-Br-Ph
77
92
9
CH
3
-(CH
2
)
2
-
2
p
-MeO-Ph
80
86
10
CH
3
-(CH
2
)
2
-
2
Ph
82
85
11
CH
3
-(CH
2
)
2
-
2
p
-Br-Ph
85
86
12
CH
3
-(CH
2
)
3
-
2
Ph
65*
88
13
CH
3
1,2-phenylene
1
Ph
93
88
14
CH
3
CH
3
CH
3
1 h
*
7
*Yield based on recovered starting material
Scheme 8C.30.
