Chemistry Reference
In-Depth Information
catalyst (0.35-1.0 mol%):
[(allyl)NiBr]
2
/
ligand*
(ratio 1:2)
additive: NaBARF (1-3 mol%)
Me
∗
X
X
H
2
CCH
2
CH
2
Cl
2
61
62
Monophosphinite Ligands
D-
gluco
D-
gluco
Ph
O
O
Ph
O
O
O
O
Me
OMe
O
O
Ar
1
2
P
AcHN
Ar
1
2
P
AcHN
OBn
67
69
a
Me
a
X = H
62%
32% ee (S)
a
93%
9% ee (S)
X = H
Ar
1
=
88%
13% ee (S)
X = Br
CF
3
35%
28% ee (S)
b
X = H
93%
45% ee (S)
X = H
b
36%
61% ee (S)
X =
i
Bu
b
CF
3
D-
allo
D-
allo
D-
allo
O
O
O
Ph
Ph
Ph
O
O
O
O
O
O
HN
AcHN
HN
OBn
OBn
OBn
O
O
O
Ar
1
2
P
Ar
1
2
P
Ar
1
2
P
O
68
O
CF
3
Ph
X = H
89%
81% ee (S)
70a
X = H
23%
82% ee (S)
40%
87% ee (S)
71a
X = H
a
X = Br
94%
89% ee (S)
X =
i
Bu
99%
74% ee (S)
X = H
95%
62% ee (S)
X = Br
19%
43% ee (S)
b
X =
i
Bu
99%
59% ee (S)
Monophosphite Ligands
O
O
c
R
ax
c
S
ax
D-
gluco
D-
allo
O
Ph
O
O
Ph
O
O
O
O
O
P
O
AcHN
O
AcHN
OBn
O
OBn
=
72
O
73
P
O
O
Ph
O
∗
d(
RR)
d(
SS)
∗
O
c
R
ax
c
S
ax
c
R
ax
c
R
ax
Ph
X = H
95%
62% ee (R)
X = H
84%
44% ee (S)
26%
2% ee (S)
99%
38% ee (S)
X = H
X = iBu
83%
19% ee (S)
c
S
ax
X = H
X = H
53%
5% ee (R)
d
(RR)
83%
30% ee (S)
d
(SS)
X = H
Scheme 9.11
Asymmetric hydrovinylation of styrene derivatives with monodentate carbohy-
drate phosphinite and carbohydrate phosphite ligands.
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