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For some recent examples, see: (a) M. Periasamy, N.S. Kumar, S. Sivakumar, V.D. Rao, C.R. Ramanathan, L. Venkatraman, J. Org. Chem. 26 (2001) 3828;(b) C. Gaul, K. Schärer, D. Seebach, J. Org. Chem. 66 (2001) 3059;(c) J.C. Barrow, P.L. Ngo, J.M. Pellicore, H.G. Selnick, P.G. Nantermet, Tetrahedron Lett. 42 (2001) 2051;(d) J. Clariana, S. Garci{dotless}́a-Granda, V. Gotor, A. Gutiérrez-Fernández, A. Luna, M. Moreno-Mañas, A. Vallribera, Tetrahedron: Asymmetry 11 (2000) 4549;(e) C. Jimeno, K.S. Reddy, L. Solà, A. Moyano, M.A. Pericàs, A. Riera, Org. Lett. 2 (2000) 3157;(f) K.S. Reddy, L. Solà, A. Moyano, M.A. Pericàs, A. Riera, Synthesis (2000) 165;(g) K. Yokoyama, T. Ishikuza, T. Kunieda, Tetrahedron Lett. 40 (1999) 6285;(h) K.S. Reddy, L. Solà, A. Moyano, M.A. Pericàs, A. Riera, J. Org. Chem. 64 (1999) 3969;(i) N. Hashimoto, T. Ishikuza, T. Kunieda, Tetrahedron Lett. 39 (1998) 6317;(j) J.M. Takacs, M.R. Jaber
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For some recent examples, see: (a) M. Periasamy, N.S. Kumar, S. Sivakumar, V.D. Rao, C.R. Ramanathan, L. Venkatraman, J. Org. Chem. 26 (2001) 3828;(b) C. Gaul, K. Schärer, D. Seebach, J. Org. Chem. 66 (2001) 3059;(c) J.C. Barrow, P.L. Ngo, J.M. Pellicore, H.G. Selnick, P.G. Nantermet, Tetrahedron Lett. 42 (2001) 2051;(d) J. Clariana, S. Garci{dotless}́a-Granda, V. Gotor, A. Gutiérrez-Fernández, A. Luna, M. Moreno-Mañas, A. Vallribera, Tetrahedron: Asymmetry 11 (2000) 4549;(e) C. Jimeno, K.S. Reddy, L. Solà, A. Moyano, M.A. Pericàs, A. Riera, Org. Lett. 2 (2000) 3157;(f) K.S. Reddy, L. Solà, A. Moyano, M.A. Pericàs, A. Riera, Synthesis (2000) 165;(g) K. Yokoyama, T. Ishikuza, T. Kunieda, Tetrahedron Lett. 40 (1999) 6285;(h) K.S. Reddy, L. Solà, A. Moyano, M.A. Pericàs, A. Riera, J. Org. Chem. 64 (1999) 3969;(i) N. Hashimoto, T. Ishikuza, T. Kunieda, Tetrahedron Lett. 39 (1998) 6317;(j) J.M. Takacs, M.R. Jaber, A.S. Vellekoop, J. Org. Chem. 63 (1998) 2742;(k) L. Solà, K.S. Reddy, A. Vidal-Ferran, A. Moyano, M.A. Pericàs, A. Riera, A. Alvarez-Larena, J.-F. Piniella, J. Org. Chem. 63 (1998) 7078.
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For a successful application of this concept, see:
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35
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In: Togni A., and Halterman R.L. (Eds). Metallocenes (1998), Wiley-VCH, Weinheim
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Metallocenes
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36
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0001283683
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Planar chiral 1,2-disubstituted ferrocenyl amino alcohols: (a) M. Watanabe, S. Araki, Y. Butsugan, M. Uemura, J. Org. Chem. 58 (1991) 2218;(b) M. Watanabe, Synlett (1995) 1050;(c) O. Delacroix, S. Picart-Goetgheluck, L. Maciejewski, J. Brocard, Tetrahedron: Asymmetry 10 (1999) 1835;(d) B. Malézieux, R. Andrés, M. Gruselle, M.-N. Rager, S. Thorimbert, Tetrahedron: Asymmetry 10 (1999) 3253.
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Planar chiral 1,2-disubstituted ferrocenyl amino alcohols: (a) M. Watanabe, S. Araki, Y. Butsugan, M. Uemura, J. Org. Chem. 58 (1991) 2218;(b) M. Watanabe, Synlett (1995) 1050;(c) O. Delacroix, S. Picart-Goetgheluck, L. Maciejewski, J. Brocard, Tetrahedron: Asymmetry 10 (1999) 1835;(d) B. Malézieux, R. Andrés, M. Gruselle, M.-N. Rager, S. Thorimbert, Tetrahedron: Asymmetry 10 (1999) 3253.
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37
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0030895210
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1-Ferrocenyl-2-aminoethanol derivatives: (a) J.A.S. Howell, K. Humphries, P. McArdle, D. Cunningham, G. Nicolosi, A. Patti, M.A. Walsh, Tetrahedron: Asymmetry 8 (1997) 1027;(b) M.R. Paleo, I. Cabeza, F.J. Sardina, J. Org. Chem. 65 (2000) 2108;(c) S. Bastin, J. Brocard, L. Pélinski, Tetrahedron Lett. 41 (2000) 7303.
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1-Ferrocenyl-2-aminoethanol derivatives: (a) J.A.S. Howell, K. Humphries, P. McArdle, D. Cunningham, G. Nicolosi, A. Patti, M.A. Walsh, Tetrahedron: Asymmetry 8 (1997) 1027;(b) M.R. Paleo, I. Cabeza, F.J. Sardina, J. Org. Chem. 65 (2000) 2108;(c) S. Bastin, J. Brocard, L. Pélinski, Tetrahedron Lett. 41 (2000) 7303.
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38
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67649445116
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N-(1-Ferrocenylalkyl)-2-aminoethanol derivatives: (a) M. Watanabe, S. Araki, Y. Butsugan, M. Uemura, Chem. Express 5 (1990) 661;(b) A. Patti, G. Nicolosi, J.A.S. Howell, K. Humphries, Tetrahedron: Asymmetry 9 (1998) 4381;(c) S. Bastin, N. Delebecque, F. Agbossou, J. Brocard, L. Pélinski, Tetrahedron: Asymmetry 10 (1999) 1647.
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N-(1-Ferrocenylalkyl)-2-aminoethanol derivatives: (a) M. Watanabe, S. Araki, Y. Butsugan, M. Uemura, Chem. Express 5 (1990) 661;(b) A. Patti, G. Nicolosi, J.A.S. Howell, K. Humphries, Tetrahedron: Asymmetry 9 (1998) 4381;(c) S. Bastin, N. Delebecque, F. Agbossou, J. Brocard, L. Pélinski, Tetrahedron: Asymmetry 10 (1999) 1647.
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39
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44949286758
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3-Amino-3-ferrocenyl-1-propanol derivatives:
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3-Amino-3-ferrocenyl-1-propanol derivatives:. Ketter A., and Herrmann R. J. Organomet. Chem. 386 (1990) 241
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Ketter, A.1
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40
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0034712326
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1-Amino-3-ferrocenyl-2-propanol derivatives: (a) A. Patti, G. Nicolosi, Tetrahedron: Asymmetry 11 (2000) 815;(b) A. Patti, G. Nicolosi, Tetrahedron: Asymmetry 11 (2000) 3687.
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1-Amino-3-ferrocenyl-2-propanol derivatives: (a) A. Patti, G. Nicolosi, Tetrahedron: Asymmetry 11 (2000) 815;(b) A. Patti, G. Nicolosi, Tetrahedron: Asymmetry 11 (2000) 3687.
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41
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0034734371
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Planar chiral 1,2-bis(ferrocenyl)-2-aminoethanol derivatives:
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Planar chiral 1,2-bis(ferrocenyl)-2-aminoethanol derivatives:. Taniguchi N., and Uemura M. J. Am. Chem. Soc. 122 (2000) 8301
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Markó, I.E.1
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For the only literature precedent on the asymmetric dihydroxylation of 1-alkenylferrocenes, see:
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For the only literature precedent on the asymmetric dihydroxylation of 1-alkenylferrocenes, see:. Jary W.G., and Baumgartner J. Tetrahedron: Asymmetry 9 (1998) 2081
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For recent structural studies on chiral ferrocenes, see: (a) U. Nettekoven, M. Wildham, H. Kalchhauser, P.C.J. Kamer, P.W.N. van Leeuwen, M. Lutz, A.L. Spek, J. Org. Chem. 66 (2001) 759;(b) Y. Wu, X. Cui, N. Zhou, M. Song, H. Yun, C. Du, Y. Zhu, Tetrahedron: Asymmetry 11 (2000) 4877;(c) C. Bolm, M. Kesselgruber, K. Muñiz, G. Raabe, Organometallics 19 (2000) 1648;(d) D. Enders, R. Peters, J. Runsink, J.W. Bats, Org. Lett. 1 (1999) 1863;(e) M. Wildham, U. Nettekoven, K. Mereiter, Tetrahedron: Asymmetry 10 (1999) 4369;(f) M.T. Reetz, E.W. Beuttenmüller, R. Goddard, M. Pastó, Tetrahedron Lett. 40 (1999) 4977;(g) W. Zhang, Y. Yoneda, T. Kida, Y. Nakatsuji, I. Ikeda, J. Organomet. Chem. 574 (1999) 19.
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For recent structural studies on chiral ferrocenes, see: (a) U. Nettekoven, M. Wildham, H. Kalchhauser, P.C.J. Kamer, P.W.N. van Leeuwen, M. Lutz, A.L. Spek, J. Org. Chem. 66 (2001) 759;(b) Y. Wu, X. Cui, N. Zhou, M. Song, H. Yun, C. Du, Y. Zhu, Tetrahedron: Asymmetry 11 (2000) 4877;(c) C. Bolm, M. Kesselgruber, K. Muñiz, G. Raabe, Organometallics 19 (2000) 1648;(d) D. Enders, R. Peters, J. Runsink, J.W. Bats, Org. Lett. 1 (1999) 1863;(e) M. Wildham, U. Nettekoven, K. Mereiter, Tetrahedron: Asymmetry 10 (1999) 4369;(f) M.T. Reetz, E.W. Beuttenmüller, R. Goddard, M. Pastó, Tetrahedron Lett. 40 (1999) 4977;(g) W. Zhang, Y. Yoneda, T. Kida, Y. Nakatsuji, I. Ikeda, J. Organomet. Chem. 574 (1999) 19.
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Only very recently, enantiopure ferrocenyl-β-amino- and bis-β-amino acids have been obtained by the diastereoselective addition of the sodium enolate of methyl acetate to chiral ferrocenylsulfinimines
-
Only very recently, enantiopure ferrocenyl-β-amino- and bis-β-amino acids have been obtained by the diastereoselective addition of the sodium enolate of methyl acetate to chiral ferrocenylsulfinimines. Adamczyc M., Reddy R.E., and Rege S.D. Synth. Commun. 30 (2000) 1389
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G.M. Sheldrick, shelxtl-PC, University of Göttingen, Germany, 1997.
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