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CH(COOMe)
2
Nu
R
R
n
R
Nu-H
L
% Conv (time)
% ee
n
L
% Conv (time)
% ee
Ph
Ph
Me
CH
2
(COOMe)
2
BnNH
2
CH
2
(COOMe)
2
40a
40a
43h
100 (6 h)
60 (24 h)
88 (10 h)
99 (
S
)
94 (
R
)
89 (
R
)
1
2
40a
40a
37 (36 h)
43 (36 h)
85 (
R
)
92 (
R
)
CH(COOMe)
2
CH(COOMe)
2
L
% Conv (time)
% regio
% ee
L
% Conv (time)
% ee
40c
100 (1 h)
80
90 (
S
)
40a
80 (24 h)
91 (
S
)
Figure 10.21
Summary of the best results obtained in the Pd-catalyzed allylic substitution of
several substrates using ligands
40-43.
R
O
% Yield
% ee
N
R
PPh
2
O
D-
xylo
a
b
c
d
i
Pr
Bn
CH
2
C
10
H
7
(
R
)-CH(CH
3
)Ph
67
64
75
17
46(
S
)
75(
S
)
49(
S
)
73(
S
)
O
O
44
Figure 10.22
Phosphine-oxazine ligands
44;
and yields and enantioselectivities obtained with
them.
D-
galacto
OR
D-
gluco
D-
gluco
OR
RO
O
O
RO
RO
PPh
2
AcO
AcO
PPh
2
O
X
PPh
2
N
N
X
RO
N
MeO
OR
OAc
OR
46
X= CH
2
;
R= Ac (45% (
S
))
47a
X= O; R= H (0%)
47b
X= O; R= Ac (0%)
45
(20% (
S
))
48a
R= H (1% (
R
))
48b
R= Ac (3% (
S
))
OAc
D-
gluco
OAc
O
O
AcO
AcO
AcO
AcO
OMe
49a
R=
t
Bu (87% (
S
))
49b
R= Bn (82% (
S
))
D-
gluco
OR
HN
N
OMe
BnO
BnO
Ph
2
P
50
(71% (
S
))
49c
R=
Ph
2
P
(86% (
S
))
O
OBn
Figure 10.23
Phosphine-imine
45-49
and phosphine-amine
50
ligands; and enantioselectivi-
ties obtained with them in the Pd-allylic alkylation of 1,3-diphenylprop-2-enyl acetate.
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