Chemistry Reference
In-Depth Information
TABLE 8B.11. Allylic Alkylations according to Scheme 8B.21 ( X = OA c )
Yield
(%)
Regioselectivity
(b/l
)
ee (%)
(Confi g.)
Entry
Substrate (R)
Ligand
Pronucleophile, Conditions
Reference
1
b
(Ph)
2 PPh
3
NaCMe(CO
2
Me)
2
, THF, − 20 ° C, 4 h
99
15:85
—
109
2
l
(Ph)
L19a
CH
2
(CO
2
Me)
2
, BSA/KOAc, CH
2
Cl
2
,
23 ° C, 18 h
87
47:53
84 (
S
)
9 5
3
l
(Ph)
L19b
CH
2
(CO
2
Me)
2
, BSA/KOAc, CH
2
Cl
2
,
23 ° C, 18 h
86
76:24
90 (
S
)
9 5
4
b
(Ph)
L19b
CH
2
(CO
2
Me)
2
, BSA/KOAc, CH
2
Cl
2
,
23 ° C, 18 h
82
66:34
88 (
S
)
9 5
5
l
(Ph)
L19c
CH
2
(CO
2
Me)
2
, BSA/KOAc, CH
2
Cl
2
, rt,
20 h
85 - 95
84:16
94 (
S
)
108
6
l
(1 - naphthyl)
L19c
CH
2
(CO
2
Me)
2
, BSA/KOAc, CH
2
Cl
2
, rt,
20 h
85 - 95
98:2
98 (
S
)
108
7
b
(Ph)
(
R
) -
MeO - MOP
NaCMe(CO
2
Me)
2
, THF,
−
30 ° C, 6 h
97
82:18
86 (
S
)
109
8
b
(4 - OMeC
6
H
4
)
(
R
) -
MeO - MOP
NaCMe(CO
2
Me)
2
, THF,
−
30 ° C, 2 h
96
90:10
87 (
S
)
109
