Chemistry Reference
In-Depth Information
TABLE 9.6. Rh - Catalyzed Asymmetric Hydroboration of Styrene (6) with Catecholborane
Me
CHPh
2
PPh
2
PCy
2
PCy
2
Fe
PPh
2
Fe
PPh
2
Fe
PPh
2
CHPh
2
(
S
,
S
)-
112
PCy
2
PPh
2
(
R
)-(
S
)-josiphos (
110
)
(
)-
111
(
R
,
R
)-
113
−
Ph
O
Ph
O
O
P
Ph
N
O
N
N
O
O
Ph
PPh
2
P
PPh
2
PPh
2
O
O
(
R
,
R
)-
114
(
S
)-quinap (
115
)
(
(
S
,
S
)-
117
R
)-
116
Me
O
Ph
Me
N
Ph
Ph
N
Me
PPh
2
N
N
N
Me
N
N
N
Fe
Ph
2
P
Fe
PPh
2
PPh
2
PPh
2
(
R
)-
118
(
S
)-
119
(
R
)-
120
(
S
)-(
R
)-
121
(
R
)-(
R
)-
122
Entry
Ligand L *
Catalyst
(mol % Rh)
Temp
( ° C)
Time
(h)
Yield
(%)
Solvent
% ee
References
1 . (
R
) - binap (
85
)
A (2)
DME
−
78
2
91
96 (
R
)
[51]
2 . (
R
) - (
S
) - josiphos
(
110
)
B (2)
DME
−
70
10
65
92 (
R
)
[52]
3 . (
−
) -
111
A (0.75)
DME
−
60
1 2
84 (
S
)
[54a]
4 . (
S,S
) -
112
A (2)
DME
rt
1
100
85 (
R
)
[54b]
A (1)
DME
3
85
[55]
5 . (
R,R
) -
113
−
35
92 (
S
)
A (2)
DME
3.5
63
[56]
6 . (
R,R
) -
114
−
78
91 (
R
)
C (0.2)
THF
20
8
75
[58]
7 . (
S
) - quinap (
115
)
91 (
S
)
C (1)
THF
rt
2
70
[59a] , [59b]
8 . (
R
) -
116
67 (
R
)
9 . (
S,S
) -
117
C (1)
THF
rt
2
70
68 (
S
)
[59c]
10. (
R
) -
118
C (1)
THF
rt
63 (
R
)
[59d]
11. (
S
) -
119
C (1)
Toluene
rt
2
73
92 (
R
)
[60]
12. (
R
) -
120
A (1)
THF
0
18
72
90 (
R
)
[61]
13. (
S
) - (
R
) -
121
A (1)
THF
20
5
91
95 (
R
)
[62]
14. (
R
) - (
R
) -
122
A (1)
THF
−
45
16
64
92 (
R
)
[63]
A, [Rh(cod)
2
]BF
4
; B, [Rh(nbd)
2
]BF
4
; C, [Rh(cod)(L * )]OTf.
