C.-Y. Chu, B.-J. Uang / Tetrahedron: Asymmetry 14 (2003) 53–55
55
Table 2. Enantioselective oxidative coupling of 2-naphthol derivatives catalyzed by chiral oxovanadium complex 1a
Entry
Time (h)
Product
Yield (%)
E.e. (%)a
1
2
3
4
16
36
11
11
8
18
9
18
48
60
4a
4b
4c
4d
4d
4d
4e
4f
93
80
96
96
90
40
93
74
54
18
25
72
73
73
72
68
b
5
6
c
7
8
9
4g
4h
Trace
Trace
ND
ND
1
0
a
Determined by HPLC with Kromasil 100-5CHI-DMB column
iPrOH/hexane=5/95, 1 mL/min).
Reaction temp: 44°C.
Reaction temp: 0°C.
(
b
c
In conclusion, enantiomerically enriched BINOLs can
be prepared using chiral vanadium complexes derived
from (S)-3-formyl-1,1%-bi-2-naphthol and (R)-a-amino
acids. The function of the phenolic hydroxyl group in
the catalyst and the mechanism of the asymmetric
coupling are currently under investigation.
2. (a) Feringa, B.; Wynberg, H. Bioorg. Chem. 1978, 7, 397;
(b) Kawashima, M.; Hirata, R. Bull. Chem. Soc. Jpn. 1993,
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1
Acknowledgements
6
4
We are grateful to the National Science Council,
Republic of China, for the support of this work.
5. (a) Hwang, D.-R.; Chen, C.-P.; Uang, B.-J. Chem. Com-
mun. 1999, 1207; (b) Chu, C.-Y.; Hwang, D.-R.; Wang,
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. LRMS (FAB) analysis for 1a (C H NO V, 526): 1051
30 21
5
+
+
(
M −H , 17), 527 (M+H , 42), 526 (M, 45), 239 (78), 154
2
(
5
(
94), 136 (100); LRMS (FAB) analysis for 3 (C H NO V,
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31 23 5
+
+
40): 1081 (M +H , 25), 541 (M+H , 60), 496 (100), 334
2
29), 239 (49), 136 (36).