2450
Q. Yao, A. R. Motta / Tetrahedron Letters 45 (2004) 2447–2451
Table 4. Activity and recyclability of Ru catalyst 6 in cross-metathesisa
Cycle
1c
Olefins (concn)
Product
O
Yieldb (%)
O
OtBu
88
30
31
tBuO
tBuO
O
(0.8M)
O
O
2c
91
18
OBu
BuO
BuO
O
(0.8M)
O
O
OtBu 30e
3d
tBuO
tBuO
(0.8M)
O
+
+
O
O
32e
81
68
( )4
tBuO
OtBu
(0.8M)
O
MeO
O
O
(0.8M)
4d
33
( )4
MeO
OMe
+
(0.8M)
a All reactions were performed in refluxing CH2Cl2 with 2.5 mol % Ru of catalyst 6.
b Refers to isolated, pure products after silica gel chromatography.
c Reaction time: 6 h.
d Reaction time: 4 h.
e See Ref. 12.
Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A.
H. J. Am. Chem. Soc. 2000, 122, 8168; Also see: (c)
Gessler, S.; Randl, S.; Blechert, S. Tetrahedron Lett. 2000,
41, 9973; For related catalysts, see: (d) Zaja, M.; Connon,
S. J.; Dunne, A. M.; Rivard, M.; Buschmann, N.; Jiricek,
J.; Blechert, S. Tetrahedron 2003, 59, 6545; (e) Wakama-
tsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 794;
(f) Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed.
2002, 41, 2403; (g) Crela, K.; Harutyunyan, S.; Mich-
rowska, A. Angew. Chem., Int. Ed. 2002, 41, 4038.
Acknowledgements
This work was supported by grants from the National
Institutes of Health (GM63522) and the Petroleum
Research Fund, administered by the American Chemi-
cal Society (36466-G1). We thank Ms. Gerri Hutson for
assistance in the synthesis of diene 16.
4. (a) Yao, Q. Angew. Chem., Int. Ed. 2000, 39, 3896; (b)
Yao, Q.; Zhang, Y. Angew. Chem., Int. Ed. 2003, 42, 3395;
(c) Yao, Q.; Zhang, Y. J. Am. Chem. Soc. 2004, 126, 74.
5. (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem.
1995, 497, 195; (b) Ahmed, M.; Barrett, A. G. M.;
Braddock, D. C.; Cramp, S. M.; Procopiou, P. A.
Tetrahedron Lett. 1999, 40, 8657; (c) Ahmed, M.; Arnauld,
T.; Barrett, A. G. M.; Braddock, D. C.; Procopiou, P. A.
References and notes
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