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For a study shedding light on the mechanistic principles that govern the reactivity of nonphosphine Ru catalysts, see: (k) Love, J. A.; Morgan, J. P.; Trnka, T. M.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 2002, 41, 4035-4037.
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(a) Kingsbury, J. S.; Garber, S. B.; Giftos, J. M.; Gray, B. L.; Okamoto, M. M.; Farrer, R. A.; Fourkas, J. T.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 2001, 40, 4251-4255.
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Kingsbury, J.S.1
Garber, S.B.2
Giftos, J.M.3
Gray, B.L.4
Okamoto, M.M.5
Farrer, R.A.6
Fourkas, J.T.7
Hoveyda, A.H.8
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See also: (b) Grela, K.; Trynowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055-9059.
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Grela, K.1
Trynowski, M.2
Bieniek, M.3
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(c) Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 2002, 41, 3835-3838.
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Connon, S.J.1
Dunne, A.M.2
Blechert, S.3
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(a) Grela, K.; Harutyunyan, S.; Michrowska, A. Angew. Chem., Int. Ed. Engl. 2002, 41, 4038-4040.
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Grela, K.1
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Michrowska, A.3
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Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. Engl. 2002, 41, 2403-2405.
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Wakamatsu, H.1
Blechert, S.2
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VanVeldhuizen, J. J.; Garber, S. B.; Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954-4955.
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0035807528
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For an alternative class of chiral Ru catalysts for olefin metathesis, see: Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225-3228.
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Seiders, T.J.1
Ward, D.W.2
Grubbs, R.H.3
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39
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0035793845
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As an example, the reaction shown in Tables 1-2 affords only polymerization products in the presence of chiral Mo-based complexes. For an overview of Mo-catalyzed enantioselective olefin metathesis, see: (a) Hoveyda, A. H.; Schrock, R. R. Chem., A Eur. J. 2001, 7, 945-950.
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Chem., A Eur. J.
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Hoveyda, A.H.1
Schrock, R.R.2
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41
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0034596810
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Sanford, M. S.; Henling, L. M.; Day, M. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 2000, 39, 3451-3453.
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Sanford, M.S.1
Henling, L.M.2
Day, M.W.3
Grubbs, R.H.4
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42
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0141893903
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note
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3 instead of OMe) could not be prepared due to susceptibility of the requisite styrene to undergo rapid polymerization.
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43
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0141928460
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note
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These are the same enantioselectivities observed with parent complex 3. In our previous report (ref 9), enantioselectivity values for non-UV-active products from reactions of 10 with 1-heptene and vinylcyclohexane were measured by HPLC/ELSD methods to be >98% ee. Subsequent investigations indicated that ELSD methods are unreliable in measuring ee values (of at least this class of compounds). Alternative approaches led us to determine subsequently that the above reactions proceed in 80-82% ee. The remaining enantioselectivities in ref 9 are correct as initially reported.
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44
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0141928461
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note
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Reaction in air with 5 mol % 3d proceeded to 50% conv after one h, presumably due to instability of the more reactive and sensitive catalyst.
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45
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0141997609
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note
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1 bond length is 2.252 Å in 3 and for 3d the two molecules in the unit cell show bond lengths of 2.267 and 2.294 Å, respectively.
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46
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0141893904
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note
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2 styrene ether.
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47
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0141928459
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note
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3-bearing Ru carbene. Moreover, recovery of the fluorinated Ru catalysts, including 3e, is more cumbersome than the derived nonfluorinated analogues.
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49
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0034053137
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For representative reports on Mo-catalyzed AROM/CM, see: (a) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829.
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Weatherhead, G.S.1
Ford, J.G.2
Alexanian, E.J.3
Schrock, R.R.4
Hoveyda, A.H.5
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50
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0034808008
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(b) La, D. S.; Sattely, E. S.; Ford, J. G.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 7767-7778.
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51
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0142046305
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(c) Tsang, W. C. P.; Jernelius, J. A.; Cortez, G. A.; Weatherhead, G. S. ; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 2591-2596.
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Schrock, R.R.5
Hoveyda, A.H.6
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52
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0032577045
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For representative reports on Mo-catalyzed ARCM, see: (a) Alexander, J. B.; La, D. S.; Cefalo, D. R.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 4041-4042.
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53
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(b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720-9721.
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Schrock, R.R.6
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54
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(c) Zhu, S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R., J. Am. Chem. Soc. 1999, 121, 8251-8259.
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Zhu, S.1
Cefalo, D.R.2
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Davis, W.M.5
Hoveyda, A.H.6
Schrock, R.R.7
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55
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0034598054
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(d) Weatherhead, G. S.; Houser, J. H.; Ford, J. G.; Jamieson, J. Y.; Schrock, R. R.; Hoveyda, A. H. Tetrahedron Lett. 2000, 41, 9553-9559.
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(e) Cefalo, D. R.; Kiely, A. F.; Wuchrer, M.; Jamieson, J. Y.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 3139-3140.
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Cefalo, D.R.1
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Schrock, R.R.5
Hoveyda, A.H.6
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(f) Kiely, A. F.; Jernelius, J.; A.; Schrock, R.; R.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 2868-2869.
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58
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(g) Dolman, S. J.; Sattely, E. S.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 2002, 124, 6991-6997.
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Dolman, S.J.1
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0001567886
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Nicolaou, K. C.; Hanko, R.; Hartwig, W., Eds.; Wiley-VCH: Weinheim
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For a discussion of the concept of "catalyst generality", see: Hoveyda, A. H. In Handbook of Combinatorial Chemistry Nicolaou, K. C.; Hanko, R.; Hartwig, W., Eds.; Wiley-VCH: Weinheim; 2002; pp 991-1016.
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Handbook of Combinatorial Chemistry
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Hoveyda, A.H.1
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60
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0141893900
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note
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The reaction of triene 37 in THF affords 38 in 65% ee; subsequent brief solvent screening proved dichloroethane to be a superior medium.
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