480
K. Tanaka
Fig. 23.2 X-ray structure of (R)-MOF-2
Table 23.2 Asymmetric epoxide ring-opening of cis-stilbene oxide catalyzed by (S)-MOF-3
O
+
50 , toluene
OH
N
H
Ph
Ph
Ph
Ph
(S)-MOF-3
NH 2
R
R
Entry
R
Time (h)
Yield (%)
Ee (%)
1
H
15
91
85
2
M e
7 0
7 8
7 5
3
MeO
63
70
62
4
F
63
95
89
5
C l
6 3
7 0
5 8
6
B r
6 3
7 2
3 1
chiral ligands. (R)-MOF-2 exhibited good enantioselectivities toward the ringopening reaction of cis-stilbene oxide with aniline or N-methyl aniline. Zhao and coworkers [7] reported synthesis of (S)-MOF-3 from (S)-6,6’-dichloro-2,2’-diethoxyl1,1’-binaphthyl-4,4’-bis(5-isophthalic acid) 3 and its good catalytic activity for
the asymmetric ring-opening reaction of cis-stilbene oxide with several anilines
(Table 23.2).
23.2.2 Oxidation of Sulfides to Sulfoxides
Tanaka and co-workers [8] described a MOF-1 catalyzed oxidation of unsymmetrical
sulfides. Various sulfides were oxidized with hydrogen peroxide or its complex with
K. Tanaka
Fig. 23.2 X-ray structure of (R)-MOF-2
Table 23.2 Asymmetric epoxide ring-opening of cis-stilbene oxide catalyzed by (S)-MOF-3
O
+
50 , toluene
OH
N
H
Ph
Ph
Ph
Ph
(S)-MOF-3
NH 2
R
R
Entry
R
Time (h)
Yield (%)
Ee (%)
1
H
15
91
85
2
M e
7 0
7 8
7 5
3
MeO
63
70
62
4
F
63
95
89
5
C l
6 3
7 0
5 8
6
B r
6 3
7 2
3 1
chiral ligands. (R)-MOF-2 exhibited good enantioselectivities toward the ringopening reaction of cis-stilbene oxide with aniline or N-methyl aniline. Zhao and coworkers [7] reported synthesis of (S)-MOF-3 from (S)-6,6’-dichloro-2,2’-diethoxyl1,1’-binaphthyl-4,4’-bis(5-isophthalic acid) 3 and its good catalytic activity for
the asymmetric ring-opening reaction of cis-stilbene oxide with several anilines
(Table 23.2).
23.2.2 Oxidation of Sulfides to Sulfoxides
Tanaka and co-workers [8] described a MOF-1 catalyzed oxidation of unsymmetrical
sulfides. Various sulfides were oxidized with hydrogen peroxide or its complex with