1304
T. Bach, A. Lemarchand
LETTER
(12) Examples for the use of 1,3-dienes as substrates in ring
Acknowledgement
closing metathesis reactions: (a) Kirkland, T. A.; Grubbs, R.
H. J. Org. Chem. 1997, 62, 7310. (b) Dvorak, C. A.;
Schmitz, W. D.; Poon, D. J.; Pryde, D. C.; Lawson, J. P.;
Amos, R. A.; Meyers, A. I. Angew. Chem. Int. Ed. 2000, 39,
1664. (c) Benningshof, J. C. J.; Blaauw, R. H.; van Ginkel,
A. E.; Rutjes, F. P. J. T.; Fraanje, J.; Goubitz, K.; Schenk, H.;
Hiemstra, H. Chem. Commun. 2000, 1465. (d) Wagner, J.;
Cabrejas, L. M. M.; Grossmith, C. E.; Papageorgiou, C.;
Senia, F.; Wagner, D.; France, J.; Nolan, S. P. J. Org. Chem.
2000, 65, 9255. (e) Snider, B. B.; Hawryluk, N. A. Org. Lett.
2001, 3, 569. (f) Garbaccio, R. M.; Stachel, S. J.; Baeschlin,
D. K.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123,
10903.
Support of our reserach by the Fonds der Chemischen Industrie is
gratefully acknowledged. A. L. thanks the Deutsche Akademische
Austauschdienst for a graduate fellowship. We thank Dr. Volker P.
Böhm (BASF AG) for a generous donation of metathesis catalysts.
References
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(19) Representative procedure for the ring closing metathesis 8
10: A solution of anilide (8d, 50 mg, 113 mol) in 5 mL
of dichloromethane was slowly added to a refluxing solution
of Grubbs’s catalyst (9a, 8.6 mg, 11.3 mol) in 220 mL of
dichloromethane. After 36 h at reflux, the reaction mixture
was cooled and the solvent was removed in vacuo. The
residue was purified by flash chromatography (pentane/
EtOAc = 9:1). Compound 10d (36 mg, 87 mol, 77%) was
obtained as a colorless liquid. 1H NMR (360 MHz, CDCl3):
= 1.10–1.47 (m, 2 H), 1.65–1.68 (m, 2 H), 2.04 (d, J = 0.7
Hz, 3 H), 2.21 (virt. q, J 8.0 Hz, 2 H), 2.70 (t, J = 6.5 Hz,
2 H), 3.67 (s, 3 H), 3.81 (s, 3 H), 3.87 (s, 3 H), 5.96 (virt. q,
(8) Andrus, M. B.; Meredith, E. L.; Soma Sekhar, B. B. V. Org.
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Chem. 1993, 58, 471. (c) Panek, J. S.; Xu, F.; Rondón, A. C.
J. Am. Chem. Soc. 1998, 120, 4113. (d) Formal syntheses:
Coutts, S. J.; Kallmerten, J. Tetrahedron Lett. 1990, 31,
4301. (e) See also: Martin, S. F.; Dodge, J. A.; Burgess, L.
E.; Limberakis, C.; Hartmann, M. Tetrahedron 1996, 52,
3229.
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Tatsuta, K. Bull. Chem. Soc. Jpn. 1992, 65, 2974.
(11) Recent Reviews: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem.
Res. 2001, 34, 18. (b) Fürstner, A. Angew. Chem. Int. Ed.
2000, 39, 3012. (c) Maier, M. E. Angew. Chem. Int. Ed.
2000, 39, 2073. (d) Grubbs, R. H.; Chang, S. Tetrahedron
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Chem., Int. Ed. Engl. 1997, 36, 2036.
J
9.1 Hz, 1 H), 6.32 (virt. t, J 10.9 Hz, 1 H), 6.99 (d,
J = 11.3 Hz, 1 H), 7.95 (s, 1 H), 8.23 (s br, 1 H). 13C NMR
(90 MHz, CDCl3): = 12.6, 22.4, 27.2, 27.4, 28.1, 28.5,
28.6, 28.8, 29.4, 29.6, 29.7, 55.9, 60.9, 61.3, 101.4, 124.1,
126.7, 127.6, 128.8, 133.5, 137.9, 141.2, 143.3, 149.4,
168.4.
Synlett 2002, No. 8, 1302–1304 ISSN 0936-5214 © Thieme Stuttgart · New York