52
X. Feng et al.
Table 2.16 Enantioselective hydrogenations of disubstituted quinolines
N
R
N
H
R
75-98% yields
86-98% ee's
95/5-99/1 dr's
R'
R'
N
R
N
H
R
74-99% yields
45-80% ee's
95/5->99/1 dr's
R'
R'
H 2
chiral diene 9j
HB(C 6 F 5 ) 2
40
41
42
43
entry product
yield (%) cis/trans ee (%)
1
41a
N
H
Ph
Ph
91
97/3
91
2
41b
N
H
Ph
Ph
94
98/2
94
3
41c
N
H
Ph
OMe
93
98/2
94
4
41d
N
H
Ph
Cl
98
>99/1
97
5
41e
N
H
Ph
O
80
98/2
87
6
41f
N
H
Ph
S
88
99/1
90
(continued)
X. Feng et al.
Table 2.16 Enantioselective hydrogenations of disubstituted quinolines
N
R
N
H
R
75-98% yields
86-98% ee's
95/5-99/1 dr's
R'
R'
N
R
N
H
R
74-99% yields
45-80% ee's
95/5->99/1 dr's
R'
R'
H 2
chiral diene 9j
HB(C 6 F 5 ) 2
40
41
42
43
entry product
yield (%) cis/trans ee (%)
1
41a
N
H
Ph
Ph
91
97/3
91
2
41b
N
H
Ph
Ph
94
98/2
94
3
41c
N
H
Ph
OMe
93
98/2
94
4
41d
N
H
Ph
Cl
98
>99/1
97
5
41e
N
H
Ph
O
80
98/2
87
6
41f
N
H
Ph
S
88
99/1
90
(continued)