2 Frustrated Lewis Pair Catalyzed Asymmetric Reactions
51
Table 2.15 Asymmetric hydrogenation of 2,3,4-trisubstituted quinolines 38
N
R"
R"'
N
H
R"
R"'
R
R
H 2
chiral diene 9l
HB(C 6 F 5 ) 2
39
76->99% yields
82-99% ee's
R'
R'
38
entry product
yield (%) ee (%)
1
39a
N
H
Me
Ph
Ph
90
90
2
39b
N
H
Me
Ph
Me
>99
92
3
39c
N
H
Me
Ph
Br
76
85
4
39d
N
H
Me
Ph
F
86
93
5
39e
N
H
Et
Ph
Ph
91
93
6
39f
N
H
n-C 6 H 13
Ph
Ph
86
89
7
39g
N
H
Me
Ph
Ph
Cl
87
93
8
39h
N
H
Me
Ph
S
78
96