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21344442252
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1st ed. (Ed.: R. H. Grubbs), Wiley-VCH, Weinheim, chap. 2 and 3
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Recent reviews on asymmetric olefin metathesis: a) A. H. Hoveyda, Handbook of Metathesis, Vol. 2, 1st ed. (Ed.: R. H. Grubbs), Wiley-VCH, Weinheim, 2003, chap. 2 and 3;
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Berlin, J.M.1
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Angew. Chem. Int. Ed 2006, 45, 7591-7595.
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b) J. J. Van Veldhuizen, D. G. Gillingham, S. B. Garber, O. Kataoka, A. H. Hoveyda, J. Am. Chem. Soc 2003, 125, 12502-12508;
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c) D. G. Gillingham, O. Kataoka, S. B. Garber, A. H. Hoveyda, J. Am Chem. Soc 2004, 126, 12288-12290;
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d) J. J. Van Veldhuizen, J. E. Campbell, R. E. Giudici, A. H. Hoveyda, J. Am. Chem. Soc. 2005, 127, 6877-6882;
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Angew. Chem. Int Ed 2007, 46, 3860-3864;
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g) G. A. Cortez, R. R. Schrock, A. H. Hoveyda, Angew. Chem. 2007, 119, 4618-4622;
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Angew. Chem. Int. Ed 2007, 46, 4534-4538;
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h) G. A. Cortez, C. A. Baxter, R. R. Schrock, A. H. Hoveyda, Org. Lett. 2007, 9, 2871-2874.
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F. Grisi, C. Costabile, E. Gallo, A. Mariconda, C. Tedesco, P. Longo, Organometallics 2008, 27, 4649-4656.
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50049095676
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53549110415
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c) S. H. Hong, A. Chlenov, M. W. Day, R. H. Grubbs, Angew. Chem. 2007, 119, 5240-5243;
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34447318400
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Angew. Chem. Int. Ed. 2007, 46, 5148-5151;
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d) J. Mathew, N. Koga, C. H. Suresh, Organometallics 2008, 27, 4666-4670;
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e) T. M. Trnka, J. P. Morgan, M. S. Sanford, T. E. Wilhelm, M. Scholl, T.-L. Choi, S. Ding, M. W. Day, R. H. Grubbs, J. Am. Chem. Soc. 2003, 125, 2546-2558.
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G. Occhipinti, H.-R. Bjørsvik, V. R. Jensen, J. Am. Chem. Soc. 2006, 128, 6952-6964.
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Such results have been obtained both by DFT calculations concerning asymmetric metathesis as well as experimental results for related achiral systems: a) C. Costabile, L. Cavallo, J. Am. Chem. Soc. 2004, 126, 9592-9600;
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J. Am. Chem. Soc.
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67749093251
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b) I. C. Stewart, D. Benitez, D. J. O'Leary, E. Tkatchouk, W. W. Day, W. A. Goddard III, R. H. Grubbs, J. Am. Chem. Soc. 2009, 131, 1931-1938;
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Goddard III, W.A.6
Grubbs, R.H.7
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36
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69949124739
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c) F. Grisi, A. Mariconda, C. Costabile, V. Bertolasi, P. Longo, Organometallics 2009, 28, 4988-4995.
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37
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0000343404
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Parallel arrangement in a methylidene species: T. M. Trnka, M. W. Day, R. H. Grubbs, Angew. Chem. 2001, 113, 3549-3552;
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Trnka, T.M.1
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0035903584
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Angew. Chem. Int. Ed. 2001, 40, 3441-3444.
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Angew. Chem. Int. Ed.
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40
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70349267328
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T. L. May, M. K. Brown, A. H. Hoveyda, Angew. Chem. 2008, 120, 7468-7472;
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Angew. Chem. Int. Ed. 2008, 47, 7358-7362.
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70350660793
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In Ref. [5a] 0.5 mol % is used for AROCM with a different substrate. ARCM with 0.75 mol%: T. W. Funk, Org. Lett. 2009, 11, 4998-5001.
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Funk, T.W.1
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T. Ritter, M. W Day, R. H. Grubbs, J. Am. Chem. Soc. 2006, 128, 11768-11769.
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Ritter, T.1
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44
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53849139133
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For a para-bromo-substituted precatalyst see: S. Leuthäußer, V. Schmidts, C. M. Thiele, H. Plenio, Chem. Eur. J. 2008, 14, 5465-5481.
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Leuthäußer, S.1
Schmidts, V.2
Thiele, C.M.3
Plenio, H.4
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45
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77953004308
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An influence of styrene additives on selectivity in ARCM has been described in Ref. [4c]
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An influence of styrene additives on selectivity in ARCM has been described in Ref. [4c].
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46
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77953018124
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Other unsymmetrically N-substituted NHC ligands with two chiral centers in their backbone show different rotational isomers (Ref. [4b]) even at room temperature
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Other unsymmetrically N-substituted NHC ligands with two chiral centers in their backbone show different rotational isomers (Ref. [4b]) even at room temperature
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47
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77952968719
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int = 0.153 R = 0.0739, Rw = 0.1511. CCDC765620 (3c) and CCDC765621 ((R)-3a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
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int = 0.153, R = 0.0739, Rw = 0.1511. CCDC765620 (3c) and CCDC765621 ((R)-3a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
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