Details

Item Description Structure
Catalog 8338 CAS 203714-71-0
Product Name Hoveyda-Grubbs Catalyst 1st Generatio
Other Name DICHLORO(O-ISOPROPOXYPHENYLMETHYLENE)(TRICYCLOHEXYLPHOSPHINE)RUTHENIUM(II);Dichloro[[2-(1-methylethoxy-O)phenyl]methylene](tricyclohexylphosphine)ruthenium
Purity 97% ee NA
Molecular Formula C28H45Cl2OPRu
Molecular Weight 600.61
Color and Form Get details by COA
Package 5g/10g and more Bulk Ordering Package
Solubility NA
Melting point 195-197 C(lit.)
Stability Yes
Risk R20/22... Safety S26/S45 Hazard NA
spectrometry Conforms to structure
HPLC Conforms to structure
Note Only for research purposes only
Technical Note

Ring-Closing Metathesis
Ring-closing metathesis has become an essential tool for C-C bond formation as demonstrated by the profound impact on total synthesis in recent years.1 The first examples date back to 1980 and involv...
William Sommer
Aldrich ChemFiles 2009,9.6, 4.
Keywords: C-C bond formation, Cyclizations, Metathesis, Ring-closing metathesis
Innumerable instances of RCM employing Grubbs and HoveydaCGrubbs first- and second-generation catalysts in small molecule and natural product syntheses have been reported. For example, the Danishefsky group employed Grubbs second-generation catalyst in the total synthesis of migrastin, a macrolide isolate from Streptomyces found to inhibit human tumor cell migration

References: (1) For example, see: Hong, S. H.; Grubbs, R. H. Org. Lett. 2007, 9, 1955. (2) For a summary of existing methods for removal of Ru-species from metathesis reactions, see: Conrad, J. C.; Fogg, D. E. Curr. Org. Chem. 2006, 10, 185. (3) (a) Maynard, H. D.; Grubbs, R. J. Tetrahedron Lett. 1999, 40, 4137. (b) Grubbs, R. H. Org. React. 2004, 22, 123. (4) Ahn, Y. M. et al. Org. Lett. 2001, 3, 1411. (5) Paquette, L. A. et al. Org. Lett. 2000, 2, 1259. (6) McEleney, K. et al. Org. Lett. 2006, 8, 2663. (7) Galan, B. R. et al. Org. Lett. 2007, 9, 1203. (8) Cho, J. H.; Kim, B. M. Org. Lett. 2003, 5 531. Gaul, C. et al. J. Am. Chem. Soc. 2003, 125, 6042. Stewart, I. C. et al. Org. Lett. 2007, 9, 1589. (1) For recent reviews, see: (a) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317. (b) Hansen, E. C.; Lee, D. Acc. Chem. Res. 2006, 39, 509. (2) For some recent examples these reactions, see: (a) N?ez, A. et al. Chem. Commun. 2006, 2690. (b) Mori, M. Adv. Synth. Catal. 2007, 349, 121. (c) Kim, B. G.; Snapper, M. L. J. Am. Chem. Soc. 2006, 128, 52.
References:
(1) For recent reviews, see: (a) Schrodi, Y.; Pederson, R. L. Aldrichimica Acta 2007, 40, 45. (b) Adv. Synth. Catal. 2007, 349, 1C268 (Olefin Metathesis Special Issue). (c) Grubbs, R. H. Tetrahedron 2004, 60, 7117. (d) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vols. 1C3. (e) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (f) Frstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (g) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 2036.
(2) With the increase of the number of reported metathesis-active Ru-catalysts, a standardized set of reactions conditions has been proposed for the purposes of comparing catalyst performance. See: Ritter, T. et al. Organometallics 2006, 25, 5740.
(3) (a) Chatterjee, A. K. et al. J. Am. Chem. Soc. 2000, 122, 3783. (b) Chatterjee, A. K.; Grubbs, R. H. Org. Lett. 1999, 1, 1751.
(4) Murelli, R. P.; Snapper, M. L. Org. Lett. 2007, 9, 1749.
(5) Stewart, I. C. et al. Org. Lett. 2007, 9, 1589.
(6) Ung, T. et al. Organometallics 2004, 23, 5399.
(7) Benitez, D.; Goddard, W. A., III. J. Am. Chem. Soc. 2005, 127, 12218.
(8) Love, J. A. et al. Angew. Chem., Int. Ed. 2002, 41, 4035.
(9) Sanford, M. S. et al. Organometallics 2001, 20, 5314.
(10) Choi, T.-L.; Grubbs, R. H. Angew. Chem. 2003, 115, 1785.
(11) Ritter, T. et al. Organometallics 2006, 25, 5740.

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