Chemistry Reference
In-Depth Information
O
O
Ph
Ph
O
O
HO
HO
O
O
O
1. MeOH.HCl
1. DMSO/(CF
3
CO)
2
O
2. L-selectride
60%
OH
HO
HO
AcHN
OMe
AcHN
2. PhCH(OMe)
2
p
TsOH, DMF
69%
AcHN
OMe
HO
12
13
11
1. KOH, EtOH
2. H
2
O
2
,Na
2
WO
4
3. LiAlH
4
4. Alkylation
1. KOH, EtOH
2. H
2
O
2
,Na
2
WO
4
3. LiAlH
4
28%
1. KOH, EtOH
2. Alkylation
1. KOH, EtOH (88%)
2. Alkylation
NR
1
R
2
O
O
Ph
Ph
O
Ph
Ph
O
O
O
O
O
1.
H
2
O
2
,Na
2
W
O
4
2. LiAlH
4
13%
OMe
HO
HO
HO
R
1
R
2
N
R
1
R
2
N
R
1
R
2
N
OMe
OMe
OMe
OH
16a,f,g,k
D-
15a,b,c,f,g,h
D-
17a
14a-k
α
-allo
D-
α
-manno
D-
α
-gluco
β
-gluco
a
R
1
=R
2
=H
b
R
1
=Et, R
2
=H
c
R
1
=R
2
=Et
d
R
1
=Pr, R
2
=H
e
R
1
=R
2
=Pr
f
R
1
=Bn, R
2
=H
g
R
1
=R
2
=Bn
h
R
1
=R
2
=-(CH
2
)
5
-
i
R
1
=R
2
=
O
j
R
1
=R
2
=CH
2
OH
k
R
1
=Ts, R
2
=H
Scheme 13.6
Synthesis of aminoalcohols
14-17.
Table 13.1
Addition of diethylzinc to benzaldehyde catalyzed by aminoalcohols
14-17.
a)
OH
O
ZnEt
2
/
14-17
∗
H
Et
Entry
Ligand
R
1
/R
2
Yield
(%)
ee (%)
(configuration.)
Entry
Ligand
R
1
/R
2
Yield
(%)
ee (%)
b)
(configuration)
1
14a
H/H
66
63
(S)
11
14k
H/Ts
55
19
(S)
2
14b
Et/H
68
20
(R)
12
15a
H/H
68
46
(S)
3
14c
Et/Et
91
53
(S)
13
15b
Et/H
81
17
(R)
4
14d
H/Pr
92
30
(R)
14
15c
Et/Et
93
26
(S)
5
14e
Pr/Pr
96
56
(S)
15
15f
H/Bn
74
14
(S)
6
14f
H/Bn
61
35
(R)
16
15g
Bn/Bn
71
32
(S)
7
14g
Bn/Bn
71
38
(S)
17
15h
(CH
2
)
5
77
28
(S)
8
14h
(CH
2
)
5
90
58
(S)
18
15i
69
28
(S)
9
14i
86
65
(S)
19
16a
H/H
94
32
(S)
10
14j
(CH
2
OH)
2
64
12
(R)
20
17a
H/H
88
21
(S)
a)
Conditions: 10 mol.% ligand, toluene, room temp.
b)
Enantiomeric excess in % and configuration of the major isomer.
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