Chemistry Reference
In-Depth Information
TABLE 8B.4. Allylic Substitutions according to Scheme 8B.16 with
C
2
- Symmetric Amines as Ligands
Ph
Ph
NH
HN
R
R
H
3
C
NH
HN
CH
3
N
N
L11a
R=H
L11b
R,R = OCH
2
CH
2
O
S
S
R
R
L9
L10
S
S
Entry
R or n
X
L
Solvent
HNu or NaNu/Conditions
Yield (%)
ee (%)
Reference
1
P h
O A c
L9
THF
NaCH(CO
2
Me)
2
[Pd(C
3
H
3
)Cl]
2
, 48 h
90
95 (
S
)
7 2
2
C H
3
OAc
L9
THF
NaCH(CO
2
Me)
2
, [Pd(C
3
H
3
)Cl]
2
, 48 h
84
47 (
S
)
7 2
3
6
OAc
ent
-
L9
THF
NaCH(CO
2
Me)
2
, [Pd(C
3
H
3
)Cl]
2
, 48 h
85
16 (
S
)
7 2
4
Ph
OAc
L10
DMF
NaCH(CO
2
Me)
2
, [Pd(C
3
H
3
)
L*
], PF
6
,
L *
, 153 ° C, 0.3 h
86
88 (+)
73
5
C H
3
OAc
L10
THF
NaCH(CO
2
Me)
2
, [Pd(C
3
H
3
)
L *
]PF
6
,
L *
, 67 ° C, 16 h
83
69 (+)
73
6
6
OAc
L10
THF
NaCH(CO
2
Me)
2
, [Pd(C
3
H
3
)
L *
]PF
6
,
L *
, 67 ° C, 2 h
63
62 ( − )
7 3
7
Ph
OCO
2
Me
L11a
THF
CH
2
(CO
2
Me)
2
, [Pd
2
(dba)
3
]CHCl
3
, BSA, KOAc, rt, 16 h
96
99 (
S
)
7 5
8
C H
3
OCO
2
Me
L11b
THF
CH
2
(CO
2
Me)
2
/Cs
2
CO
3
, [Pd(C
3
H
3
)Cl]
2
, AgSbF
6
, 0 ° C, 4 days
73
94 (
S
)
7 5
