Debra J. Wallace
COMMUNICATIONS
Chem. Soc. 2000, 122, 8168; d) S. Gessler, S. Randl, S.
Blechert, Tetrahedron Lett. 2000, 41, 9973; e) J. S.
Kingsbury, J. P. A. Harrity, P. J. Bonitatebus, Jr., A. H.
Hoveyda, J. Am. Chem. Soc. 1999, 121, 791.
[9] For one example of the failure of 5a in a RCM reaction
see R. N. Chapman, P. S. Arora, Org. Lett. 2006, 8,
5825.
[10] a) T. J. Katz, N. Acton, Tetrahedron Lett. 1976, 17,
4251; b) T. J. Katz, S. J. Lee, M. A. Shippey, J Mol.
Catal. 1980, 8, 219.
[5] For other ruthenium olefin metathesis catalysts see
refs.[1,2] and, inter alia: a) A. Fꢁrstner, J. Grabowski,
C. W. Lehmann, J. Org. Chem. 1999, 64, 8275; b) J.
Huang, E. D. Stevens, S. P. Nolan, J. L. Petersen, J. Am.
Chem. Soc. 1999, 121, 2674; c) M. Scholl, T. M. Trnka,
J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40,
2247; d) L. Jafarpour, H. J. Schanz, E. D. Stevens, S. P.
Nolan, Organometallics 1999, 18, 5416; e) T. Weskamp,
F. J. Kohl, W. Hieringer, D. Gleich, W. A. Herrmann,
Angew. Chem. 1999, 111, 2573; Angew. Chem. Int. Ed.
1999, 38, 2416; f) A. Fꢁrstner, O. Guth, A. Duffels, G.
Seidel, M. Liebl, B. Gabor, R. Mynott, R. Chem. Eur.
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Blechert, Angew. Chem. 2002, 114, 832; Angew. Chem.
Int. Ed. 2002, 41, 794;; i) H. Wakamatsu, S. Blechert,
Angew. Chem. 2002, 114, 2509; Angew. Chem. Int. Ed.
2002, 41, 2403; j) A. Michrowska, R. Bujok, S. Haru-
tyunyan, V. Sashuk, G. Dolgonos, K. Grela, J. Am.
Chem. Soc. 2004, 126, 9318; k) M. Bicnick, R. Bujok,
M. Cabaj, N. Lugan, G. Lavigne, D. Arlt, K. Grela, J.
Am. Chem. Soc. 2006, 128, 13652.
[11] Z. Wu, S. T. Nguyen, R. H. Grubbs, J. W. Ziller, J. Am.
Chem. Soc. 1995, 117, 5503.
[12] W. Weck, B. Mohr, B. R. Maughon, R. H. Grubbs, Mac-
romolecules 1997, 30, 6430.
[13] Reactions were monitored by HPLC and/or NMR. To
allow for convenient analysis, catalyst loadings for each
substrate were chosen to give reaction times in the
order of hours. A preliminary evaluation of the reactiv-
ity of each substrate with catalyst 1 was used to guide
this choice.
[14] Compounds 14, 16 and 23 were prepared by addition of
allylmagnesium chloride, vinylmagnesium bromide and
propargylmagnesium bromide to 4-bromobenzaldehyde
respectively, followed by reaction of the resulting alco-
hol with allyl bromide and sodium hydride. New com-
pounds were characterised by standard methods.
[15] a) D. J. Wallace, C. J. Cowden, D. J. Kennedy, M. S.
Ashwood, I. F. Cottrell, U. H. Dolling, Tetrahedron
Lett. 2000, 41, 2027; b) D. J. Wallace, J. M. Goodman,
D. J. Kennedy, A. J. Davies, C. J. Cowden, M. S. Ash-
wood, I. F. Cottrell, U. H. Dolling, P. J. Reider, Org.
Lett. 2001, 3, 671; c) D. J. Wallace, Tetrahedron Lett.
2005, 46, 591; d) D. J. Wallace, J. Mol. Catal. A 2006,
254, 78.
[16] For reviews of ring-closing enyne metathesis see:
a) C. S. Poulsen, R. Madsen, Synthesis 2003, 1; b) S. T.
Diver, A. J. Geissert, Chem. Rev. 2004, 104, 1317; c) M.
Mori, Adv. Synth. Catal. 2007, 349, 121.
[17] Enyne methathesis reactions are often run under ethyl-
ene atmospheres to promote turnover (M. Mori, N. Sa-
kakibara, A. Kinoshita, A. J. Org. Chem. 1998, 63,
6082). To avoid confounding results ethylene was not
used in this study and may have compromised the reac-
tions with catalyst 2 compared to literature results.
[6] a) H. Clavier, S. P. Nolan, Chem. Eur. J. 2007, 13, 8029;
b) M. Bieniek, A. Michrowska, D. L. Usanov, K. Grela,
Chem. Eur. J. 2008, 14, 806.
[7] a) H. Katayama, H. Urushima, T. Nishioka, C. Wada,
M. Nagao, F. Ozawa, Angew. Chem. 2000, 112, 4687;
Angew. Chem. Int. Ed. 2000, 39, 4513; b) P. A. van der
Schaaf, R. Kolly, H. J. Kirner, F. Rime, A. Muhlebach,
A. Hafner, J. Organomet. Chem. 2000, 606, 65; c) J.
Louie, R. H. Grubbs, Organometallics 2002, 21, 2153;
d) H. Katayama, M. Nagao, F. Ozawa, Organometallics
2003, 22, 586.
[8] a) P. A. van der Schaaf, A. Hafner, A. Muhlebach,
Patent WO 99/00396, 1999; b) catalysts 5a and 6 are
available from Strem in research quantities.
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ꢀ 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2009, 351, 2277 – 2282