82
X. Feng et al.
Table 2.40 Mannich-type reaction with different pronucleophiles and electrophiles
R 1
H
O
R 2
+
N
PG
Ar
chiral diene 9 (10 mol %)
HB(C 6 F 5 ) 2 10 (10 mol %)
base (20 mol %)
R 2
O
R 1
HN
PG
Ar
81
85
86
entry catalyst
product
yield (%) anti/syn ee (%)
1
9c+PMP 2
86a
HN
Boc
Ph
O
F
98
>20/1
92
2
9c+PMP 2
86b
HN
Boc
Ph
O
O
99
>20/1
90
3
9c+PMP 2
86c
HN
Boc
Ph
O
99
10/1
84
4
9c+PMP 2
86d
HN
Boc
Ph
Ph
O
97
-72
5
9a+PMP 2
86e
HN
Boc
Ph
O
87
>20/1
84
6
9c+PMP 2
86f
HN
Boc
O
F
96
>20/1
96
7
9c+PMP 2
86g
HN
Boc
O
O
98
>20/1
74
8
9c+PMP 2
86h
HN
Cbz
Ph
O
99
>20/1
94
9
9c+Barton’s base
86i
HN
Boc
Ph
S
O
Me
63
7/1
70
10
9h+Barton’s base
86j
HN
Boc
Ph
O
O
Me
98
10/1
54
11
9a+PMP 2
86k
HN
Ts
O
73
3/1
anti: 16
syn: 66