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Enantioselective hydrocyanation of aromatic vinyl compounds, US Patent 5,175,335, 1992, The DuPont Company.
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(a) Enantioselective hydrocyanation of aromatic vinyl compounds, RajanBabu, T. V.; Casalnuovo, A. L. US Patent 5,175,335, 1992, The DuPont Company.
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M.P. Doyle JAI Greenwich
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T.V. RajanBabu, A.L. Casalnuovo, and T.A. Ayers M.P. Doyle Ligand Tuning in Asymmetric Catalysis: Hydrocyanation and Hydrogenation Reactions Advances in Catalytic Processes Vol. 2 1997 JAI Greenwich 1 41
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B.L. Feringa, M. Pineschi, L.A. Arnold, R. Ombos, and A.H.M. de Vries Angew. Chem. Int., Ed. 36 2001 2620 2623
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45
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20444431695
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Ph.D. Thesis, The Ohio State University. See also: Ref. 21(a), Supporting Information.
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2P-Cl gave low yield and selectivity (17%, 5% ee). Park H.; Ph.D. Thesis, 2000, The Ohio State University. See also: Ref. 21(a), Supporting Information.
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Park, H.1
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49
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0008451370
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3) for (S)- 2c of 74% ee. Hayashi reported a value of +5.66 (neat) for material estimated to be 80% ee. See: (a) T. Hayashi, M. Konishi, M. Fukushima, K. Kanehira, T. Hioki, and M.J. Kumada Org. Chem. 48 1983 2195 2202
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50
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20444435699
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US Patent 4,912,274, 1990.
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(b) Wilke reported +6.18 for a sample (∼85% ee) obtained by hydrovinylation of 4-isobutylstyrene. Wilke, G.; Monkiewicz, J.; Kuhn, H. US Patent 4,912,274, 1990.
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0344848128
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D values may have to be revised
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54
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20444432513
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note
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We thank Dr. Xiufeng Sun for this experiment.
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55
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84981909682
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Hydrovinylation of norbornene is one of the first asymmetric, metal-catalyzed C-C bond-forming reactions reported. See: B. Bogdanovíc, B. Henc, A. Löser, B. Meister, H. Pauling, and G. Wilke Angew. Chem. Int., Ed. Engl. 12 1973 954 964 For more recent results from the Wilke group, see Ref. 20b
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Bogdanovíc, B.1
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For hydrovinylation of norbornadiene, see, Ref. 29 and, S.M. Pillai, G.L. Tembe, and M. Ravindranathan J. Mol. Catal. 84 1993 77 86
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Pillai, S.M.1
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59
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20444487914
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note
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For identification of the relative and absolute configuration of (-)- 18 and relative configuration 19, see Ref. 22. The absolute configuration of 19 has not been determined.
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65
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37049087172
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Hydroalkenylation: F. Ozawa, Y. Kabatake, A. Kubo, and T. Hayashi J. Chem. Soc., Chem. Commun. 1994 1323 1324
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Addition Polymers Derived from Norbornene-Functional Monomers and Process Therefor, US Patent 5,571,881, 1996, The B.F. Goodrich Company.
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(a) Polymerization of norbornene by Ni(II)-complexes has been extensively studied by Goodall et al. For a leading Ref. see, (a) Addition Polymers Derived from Norbornene-Functional Monomers and Process Therefor, Goodall, B. L.; Benedikt, G. M.; McIntosh, I. L. H.; Barnes, D. A.; Rhodes, L.F., US Patent 5,571,881, 1996, The B.F. Goodrich Company.
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B.L. Goodall Cycloaliphatic polymers via late transition metal catalysis B. Rieger L.S. Baugh S. Kacker S. Striegler Late Transition Metal Polymerization Catalysis 2003 Wiley-VCH Weinheim 101 154
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For other examples, see Ref. 24.
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For other examples, see Ref. 24.
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70
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20444432915
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