Chemistry Reference
In-Depth Information
1-Np
R
X
R
O
COX
P
PPh
2
Ph
N
PPh
2
H
O
Fe
H
Fe
N
PPh
2
P
P
PPh
2
Ph
COX
P
O
1-Np
(
S,S
)-
L5
(
R
,
R
)-
DXP A
(
L6a
) R = Me, X = S
(
R
,
R
)-
DXP B
(
L6b
) R = H, X = CMe
2
L7
L8a
X = OMe,
L8b
X = O
i
-Pr,
L8b
X = N(
i
-Pr)
2
Pronucleophile/Conditions
a
Entry
R or n
X
L
Solvent
Yield (%)
ee (%)
Reference
1
P h
O A c
(
R
,
R
) -
DPBBA - 1
CH
2
Cl
2
CH
2
(CO
2
Me)
2
/Cs
2
CO
3
9
52 (
R
)
6 3
2
C H
3
OCO
2
Me
(
R
,
R
) -
DPBBA - 1
CH
2
Cl
2
CH
2
(CO
2
Me)
2
/Cs
2
CO
3
98
92
b
(
R
)
6 3
3
6
OCO
2
Me
(
R
,
R
) -
DPBBA - 1
CH
2
Cl
2
NaCH(CO
2
Me)
2
/N(
n
- Hex)
4
Br
86
96 (
S
)
6 3
4
6
OCO
2
t
- Bu
L5
CH
2
Cl
2
CH
2
(CO
2
Me)
2
, BSA, LiOAc
64
> 99 (
S
)
6 6
5
Ph
OAc
(
R
,
R
) -
DXP A
CH
2
Cl
2
CH
2
(CO
2
Me)
2
, BSA, KOAc, 0 ° C, 24 h
100
c
97 (
R
)
6 8
6
C H
3
OAc
(
R
,
R
) -
DXP A
CH
2
Cl
2
CH
2
(CO
2
Me)
2
, BSA, KOAc, 0 ° C, 3 h
100
c
68 (
S
)
6 8
7
6
O A c
(
R
,
R
) -
DXP A
THF
CH
2
(CO
2
Me)
2
, BSA, KOAc, − 20 ° C, 4 h
100
c
93 (
S
)
6 8
8
C H
3
OAc
(
R
,
R
) -
DXP B
THF
CH
2
(CO
2
Me)
2
, BSA, KOAc, − 10 ° C, 15 h
100
c
82 (
S
)
6 8
9
6
O A c
(
R
,
R
) -
DXP B
THF
CH
2
(CO
2
Me)
2
, BSA, KOAc, 20 ° C, 3 min
100
c
77 (
S
)
6 8
16
Ph
OAc
L7
CH
2
Cl
2
CH
2
(CO
2
Me)
2
, BSA, KOAc, 0 ° C, 3 h
84
73 (
R
)
7 0
17
CH
3
OAc
L7
CH
2
Cl
2
CH
2
(CO
2
Me)
2
, BSA, KOAc,
−
10 ° C, 24 h
76
9 (+)
70
18
6
OAc
L7
CH
2
Cl
2
CH
2
(CO
2
Me)
2
, BSA, KOAc, 25 ° C, 24 h
77
26 (
R
)
7 0
19
Ph
OAc
L8b
CH
2
Cl
2
CH
2
(CO
2
Me)
2
, BSA, KOAc, 0 ° C, 10 h
63
94 (
S
)
7 1
20
CH
3
OAc
L8a
CH
2
Cl
2
CH
2
(CO
2
Me)
2
, BSA, KOAc, 0 ° C, 10 min
>
90
12 (
S
)
7 1
21
6
OAc
L8a
CH
2
Cl
2
CH
2
(CO
2
Me)
2
, BSA, KOAc,
−
50 ° C, 1 h
>
90
83 (
R
)
7 1
a
[Pd( π - C
3
H
5
)Cl]
2
was used as Pd source.
b
ee of 94% was obtained with
DPPBA - 2
.
c
Conversion.
