5 For chelating ether, see: S. B. Garber, J. S. Kingsbury, B. L. Gray and
A. H. Hoveyda, J. Am. Chem. Soc., 2000, 122, 8268; for chelating
amines, see: T. Ung, A. Hejl, R. H. Grubbs and Y. Schrodi,
Organometallics, 2004, 23, 5399; for chelating imines, see: (a) A. Hejl,
M. W. Day and R. H. Grubbs, Organometallics, 2006, 25, 6149; (b)
C. Slugovc, D. Burtscher, F. Stelzer and K. Mereiter, Organometallics,
2005, 24, 2255.
6 A rate enhancement was found when an alkoxide was exchanged for a
carboxylate in analogs to 3, see: T. S. Halbach, S. Mix, D. Fischer,
S. Maechling, J. O. Krause, C. Sievers, S. Blechert, O. Nuyken and M.
R. Buchmeiser, J. Org. Chem., 2005, 70, 4687.
Wiley-VCH, Weinheim, Germany, 2003, vol. 2, ch. 2.3; (b)
R. R. Schrock and A. H. Hoveyda, Angew. Chem., Int. Ed., 2003, 42,
4592; (c) A. H. Hoveyda and R. R. Schrock, Chem.–Eur. J., 2001, 7,
945.
12 For Ru-based catalysts, see: (a) J. M. Berlin, S. D. Goldberg and
R. H. Grubbs, Angew. Chem., Int. Ed., 2006, 45, 7591; (b) T. W. Funk,
J. M. Berlin and R. H. Grubbs, J. Am. Chem. Soc., 2006, 128, 1840; (c)
T. J. Seiders, D. W. Ward and R. H. Grubbs, Org. Lett., 2001, 3, 3225;
(d) J. J. Van Veldhuizen, D. G. Gillingham, S. B. Garber, O. Kataoka
and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 12502; (e) J. J. Van
Veldhuizen, S. B. Garber, J. S. Kingsbury and A. H. Hoveyda, J. Am.
Chem. Soc., 2002, 124, 4954.
7
13 For Mo-based catalysts, see: (a) A.-L. Lee, S. J. Malcolmson, A. Puglisi,
R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2006, 128, 5153;
(b) W. C. P. Tsang, J. A. Jernelius, G. A. Cortez, G. S. Weatherhead,
R. R. Schrock and A. H. Hoveyda, J. Am. Chem. Soc., 2003, 125, 2591;
(c) S. L. Aeilts, D. R. Cefalo, P. J. Bonitatebus, J. H. Houser,
A. H. Hoveyda and R. R. Schrock, Angew. Chem., Int. Ed., 2001, 40,
1452; (d) S. S. Zhu, D. R. Cefalo, D. S. La, J. Y. Jamieson, W. M. Davis,
A. H. Hoveyda and R. R. Schrock, J. Am. Chem. Soc., 1999, 121, 8251;
(e) J. B. Alexander, D. S. La, D. R. Cefalo, A. H. Hoveyda and
R. R. Schrock, J. Am. Chem. Soc., 1998, 120, 4041.
14 Very recently, Rh(I) prolinate was reported to asymmetrically
polymerize carbenes, see: D. G. H. Hetterscheid, C. Hendriksen,
W. I. Dzik, J. M. M. Smits, E. R. H. van Eck, A. E. Rowan, V. Busico,
M. Vacatello, V. Van Axel Castelli, A. Segre, E. Jellema,
T. G. Bloemberg and B. de Bruin, J. Am. Chem. Soc., 2006, 128,
9746.
.
8 T. Ritter, A. Hejl, A. G. Wenzel, T. W. Funk and R. H. Grubbs,
Organometallics, 2006, 25, 5740.
9 (a) E. L. Dias, S. T. Nguyen and R. H. Grubbs, J. Am. Chem. Soc.,
1997, 119, 3887; (b) J. P. Morgan and R. H. Grubbs, Org. Lett., 2000, 2,
3153.
10 (a) B. Schmidt, Eur. J. Org. Chem., 2004, 1865; (b) S. H. Hong,
D. P. Sanders, C. W. Lee and R. H. Grubbs, J. Am. Chem. Soc., 2005,
127, 17160.
11 For reviews of asymmetric olefin metathesis reactions, see: (a)
A. H. Hoveyda, in Handbook of Metathesis, ed. R. H. Grubbs,
15 The synthesis of catalyst 6 is similar to the synthesis of catalyst 5,
starting from 2 and proline. The synthesis, characterization, and activity
will be reported later.
2828 | Chem. Commun., 2007, 2826–2828
This journal is ß The Royal Society of Chemistry 2007