Chemistry Reference
In-Depth Information
TABLE 8B.19. Asymmetric Allylic Alkylations of 2 - Methyltetralones
O
OSnBu
3
R
O
R
R
Allyl substrate
[Pd(
π
-C
3
H
5
)Cl]
2,
(
S
,
S
)-
DPPBA-1
,
DME, rt
LDA
Bu
3
Sn Cl
Allyl
n
n
n
Entry
R
n
Allylic Substrate
Product
Yield (%)
ee (%)
1
CH
3
1
99
88
OAc
O
2
CH
3
1
84
90
OCOOMe
O
3
a
CH
3
1
72
82
OCOOMe
O
R
R
4
CH
3
1
41
OPO(OEt)
2
O
>
95
5
i -
Pr
1
99
35
OAc
O
i
Pr
6
CH
3
0
OAc
O
79
38
7
CH
3
2
90
6
OAc
O
a
R = (CH
2
)
3
OSi(
t
- Bu)Ph
2
O
O
O
PPh
2
PPh
2
NH
HN
HN
NH
OC
Fe
N
PPh
2
CO
P
P
P
Ph
2
P
Fe
Ph
2
Ph
2
Ph
2
(
S
,
S
)-
DPPBA-1
(
L1a
)
(
S
)-
t
-
Bu
-
PHOX
(
L31
)
(
S
)-
BINAP
(
L23a
)
L28
Figure 8B.14.
Some of the ligands used in allylic alkylations of ketones.
