Chemistry Reference
In-Depth Information
R'
R'
OH
OH
N
N
H
N
N
H
Q
, R' = OMe, quinine
CD
, R' = H, cinchonidine
QD
, R' = OMe, quinidine
CN
, R' = H, cinchonine
N
Et
Et
Et
N
N
O
O
O
H
H
H
H
H
OMe
MeO
H
O
O
MeO
DHQD-PHN(
26
)
(DHQD)
2
AQN(
27
)
O
R
O
R
OH
OMe
R'
R'
O
n
n
MeOH, PhMe, or PhMe/PhCl
R
R
O
O
29
28
Method A (Oada):
CN
,
QD
,or
QN
(10 mol %), > 95% yield, 25-70% ee
Method B (Bolm):
QD
,or
QN
(110 mol %), 84-99% yield, 84-98% ee
Method C (Deng):
27
(5-30 mol %), 56-99% yield, 82-98% ee
Method D (Bolm):
QD
(10 mol %), pempidine (1 equiv), 96-98% yield, 74-92% ee
O
O
O
R
R
R
27
(15 mol %)
R'OH
OH
OR'
O
+
OR'
OH
Ether, -24°C
O
30
O
O
31
32
O
O
O
26
or
27
(10-20 mol %)
R'OH
O
R
R
R
R
H
2
O
OR'
+
OH
O
O
PN
PN
PHN
Ether, -78 to 0°C
PHN
33
O
S
-33
O
R
-34
S
-35
O
O
O
O
R
R
R
R
27
(10 mol %), R'OH
H
2
O
OR' +
O
OH
O
O
O
Ether, -78°C
OH
OH
O
R
-37
S
-36
O
S
-38
36
Scheme 2B.5.
