Chemistry Reference
In-Depth Information
TABLE 7.13. Asymmetric Hydrogenation of Amino Ketones
O
OH
Metal-ligand complex
H
2
∗
X
X
R
R
n
n
Reaction
Conditions
% ee
(Confi g.)
Catalyst
R
X
n
S
/
C
Reference
(
R
) - (
S
) - BPPFOH - Rh
(3,4) -
(OH)
2
Ph
NHMe · HCl
1
100
NEt
3
,
MeOH,
rt, 50 atm
H
2
95 (
R
)
12b
(2
S
,4
S
) - MCCPM - Rh
Ph
NEt
2
· HCl
1
100,000
NEt
3
,
MeOH,
50 ° C,
20 atm H
2
96 (
S
)
268
(
S
) - Cp,Cp -
oxoProNOP - Rh
Ph
NMe
2
· HCl
1
200
MeOH,
20 ° C,
50 atm H
2
96 (
S
)
234e
(
S
) - Cp,Cp -
oxoProNOP - Rh
Me
NMe
2
· HCl
1
200
MeOH,
20 ° C,
50 atm H
2
97 (
S
)
234e
(
S
) - Cp,Cp - IndoNOP -
Rh
Ph
NMe
2
· HCl
1
200
Toluene,
20 ° C,
50 atm H
2
99 (
S
)
234g
Ph
NMe
2
· HCl
2
200
Toluene,
20 ° C,
20 atm H
2
234g
(
S
) - Cy,Cy -
oxoProNOP - Rh
93 (
R
)
(2
S
,4
S
) - MCCPM - Rh
Ph
N(Me)Bn · HCl
2
1,000
MeOH,
50 ° C,
30 atm H
2
91 (
R
)
232f
(
S
) - Cy,Cy -
oxoProNOP - Rh
Ph
NMe
2
· HCl
3
200
Toluene,
80 ° C,
50 atm H
2
92 (
R
)
234e
(
S
c
,
R
p
) -
DuanPhos - Rh
4 - Br - Ph
NHMe · HCl
2
200
MeOH,
50 ° C,
50 bar H
2
,
K
2
CO
3
>
99 (
S
)
266
(
S
c
,
R
p
) -
DuanPhos - Rh
4 - OMePh
NHMe · HCl
2
200
MeOH,
50 ° C,
50 bar H
2
,
K
2
CO
3
>
99 (
S
)
266
(
S
) - BINAPINE - Rh
Ph
NHMe · HCl
1
4,000
MeOH, rt,
50 atm
H
2
,
K
2
CO
3
94 (
S
)
267
