Chemistry Reference
In-Depth Information
Table 8.4 Hydrogenation of hex-1-en-2-yl benzoate, dimethyl itaconate, and
N -acetylphenylethenamine with monophosphite ligands 39 - 47.
Entry
Product
Ligand
Conversion (%)
ee (%)
86 a) (S)
1
39b
100
2
41b
100
39 (S)
*
n-C 4 H 9
OBz
3
42b
100
68 (S)
4
43b
100
51 (S)
5
39a
100
99 (S)
6
39b
100
93 (R)
7
40a
100
97 (S)
8
41a
100
78 (S)
9
44a
100
83 (S)
CO 2 Me
10
MeO 2 C
*
4b
45a
100
92 (S)
11
46a
100
99 (S)
12
46b
100
>
99 (R)
13
46d
100
>99 (R)
14
47b
100
99 (S)
15
39b
100
94 (S)
16
47b
100
95 (S)
*
NHAc
17
47d
100
99 (S)
a) 94% (S) using hex-1-en-2-yl furan-2-carboxylate.
D- gluco
D- allo
D- manno
D- galacto
O
O
R
R
O
P
O
O
O
O
P
O
O
O
O
O
O
O
O
O
O
O
O
O O
O
O
O
R
O O
O
P
O
O
O
O
O
P
R
43
39 R,R= isopropylidene
40 R,R= ciclohexylidene
42
41
O =
O
a ( S ) ax
b ( R ) ax
D- psico
D- fructo
O
O
O
P
O
O
O
O
O
R
O
O
R
O
R
O
O
R
R
O
P
O =
R
O
O
c ( S ) ax
d ( R ) ax
O
R
R
O
O
O
O
44 R,R= isopropylidene
45 R,R= cyclohexylidene
46 R,R= isopropylidene
47 R,R= cyclohexylidene
Figure 8.6 Monophosphite ligands 39 - 47.
 
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