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0029945485
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For an example of high-symmetry complex formation from a low-symmetry ligand, see: Davies, H. M. L., Bruzinski, P. R.; Lake, D. H.; Kong, N., Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897.
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Girard, C.1
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Kagan, H.B.1
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Springer: New York
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Review: (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2923. (b) Kagan, H. B. Synlett 2001, 888. (c) Kagan, H. B.; Luukas, T. O. In Comprehensive Asymmetric Catalysis I-III; Springer: New York, 1999; Vol. 1, pp 101-118. Selected recent examples: (d) Steigelmann, M.; Nisar, Y.; Rominger, F.; Goldfuss, B. Chem. Eur. J. 2002, 8, 5211. (e) Buono, F.; Walsh, P. J.; Blackmond, D. G. J. Am. Chem. Soc. 2002, 124, 13652. (f) Balsells, J.; Davis, T. J.; Carroll, P.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10836.
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Kagan, H.B.1
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Review: (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2923. (b) Kagan, H. B. Synlett 2001, 888. (c) Kagan, H. B.; Luukas, T. O. In Comprehensive Asymmetric Catalysis I-III; Springer: New York, 1999; Vol. 1, pp 101-118. Selected recent examples: (d) Steigelmann, M.; Nisar, Y.; Rominger, F.; Goldfuss, B. Chem. Eur. J. 2002, 8, 5211. (e) Buono, F.; Walsh, P. J.; Blackmond, D. G. J. Am. Chem. Soc. 2002, 124, 13652. (f) Balsells, J.; Davis, T. J.; Carroll, P.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10836.
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Review: (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2923. (b) Kagan, H. B. Synlett 2001, 888. (c) Kagan, H. B.; Luukas, T. O. In Comprehensive Asymmetric Catalysis I-III; Springer: New York, 1999; Vol. 1, pp 101-118. Selected recent examples: (d) Steigelmann, M.; Nisar, Y.; Rominger, F.; Goldfuss, B. Chem. Eur. J. 2002, 8, 5211. (e) Buono, F.; Walsh, P. J.; Blackmond, D. G. J. Am. Chem. Soc. 2002, 124, 13652. (f) Balsells, J.; Davis, T. J.; Carroll, P.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10836.
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Review: (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2923. (b) Kagan, H. B. Synlett 2001, 888. (c) Kagan, H. B.; Luukas, T. O. In Comprehensive Asymmetric Catalysis I-III; Springer: New York, 1999; Vol. 1, pp 101-118. Selected recent examples: (d) Steigelmann, M.; Nisar, Y.; Rominger, F.; Goldfuss, B. Chem. Eur. J. 2002, 8, 5211. (e) Buono, F.; Walsh, P. J.; Blackmond, D. G. J. Am. Chem. Soc. 2002, 124, 13652. (f) Balsells, J.; Davis, T. J.; Carroll, P.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10836.
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For example: (a) Shibasaki, M.; Sasai, H. Top. Stereochem. 1999, 22, 201-225. (b) Shibasaki, M.; Sasai, H. Adv. Asymmetric Synth. 1998, 3, 191-233.
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For reviews on nitrogen-containing ligands for asymmetric catalysis, see: (a) Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159. (b) McCarthy, M.; Guiry, P. J. Tetrahedron 2001, 57, 3809.
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For other derivatives within this class not shown, see: (a) Tucker, S. C.; Brown, J.; Oakes, J.; Thornthwaite, D. Tetrahedron 2001, 57, 2545. (b) Brunner, H.; Olschewski, G.; Nuber, B. Synthesis 1999, 3, 429. (c) Tsue, H.; Fujinami, H.; Itakura, T.; Tsuchiya, R.; Kobayashi, K.; Takahashi, H.; Hirao, K. J. Chem. Soc., Perkin Trans. 1 1998, 3677. (d) Meyers, A. I.; Lutomski, K. A. J. Am. Chem. Soc. 1982, 104, 879.
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For other derivatives within this class not shown, see: (a) Tucker, S. C.; Brown, J.; Oakes, J.; Thornthwaite, D. Tetrahedron 2001, 57, 2545. (b) Brunner, H.; Olschewski, G.; Nuber, B. Synthesis 1999, 3, 429. (c) Tsue, H.; Fujinami, H.; Itakura, T.; Tsuchiya, R.; Kobayashi, K.; Takahashi, H.; Hirao, K. J. Chem. Soc., Perkin Trans. 1 1998, 3677. (d) Meyers, A. I.; Lutomski, K. A. J. Am. Chem. Soc. 1982, 104, 879.
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For other derivatives within this class not shown, see: (a) Tucker, S. C.; Brown, J.; Oakes, J.; Thornthwaite, D. Tetrahedron 2001, 57, 2545. (b) Brunner, H.; Olschewski, G.; Nuber, B. Synthesis 1999, 3, 429. (c) Tsue, H.; Fujinami, H.; Itakura, T.; Tsuchiya, R.; Kobayashi, K.; Takahashi, H.; Hirao, K. J. Chem. Soc., Perkin Trans. 1 1998, 3677. (d) Meyers, A. I.; Lutomski, K. A. J. Am. Chem. Soc. 1982, 104, 879.
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For other derivatives within this class not shown, see: (a) Tucker, S. C.; Brown, J.; Oakes, J.; Thornthwaite, D. Tetrahedron 2001, 57, 2545. (b) Brunner, H.; Olschewski, G.; Nuber, B. Synthesis 1999, 3, 429. (c) Tsue, H.; Fujinami, H.; Itakura, T.; Tsuchiya, R.; Kobayashi, K.; Takahashi, H.; Hirao, K. J. Chem. Soc., Perkin Trans. 1 1998, 3677. (d) Meyers, A. I.; Lutomski, K. A. J. Am. Chem. Soc. 1982, 104, 879.
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note
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In this and all subsequent crystal structures, the asymmetric unit cell is always paired with its mirror image. That is, the single crystals are (presumably) optically inactive.
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Zirconium amido complexes 14-18 immediately decompose to free ligand (1) upon contact with water.
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2542579637
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a, values for pyridinium tosylate and dimethylanilinium tosylate are 5.21 and 5.20, respectively. March, J. Advanced Organic Chemistry, 3rd. ed.; Wiley: New York, 1985. Unpublished results of W. P. Jencks.
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The axially chiral bis(dimethylamino) binaphthylene derivative reported by Salvadori catalyzes the diethyl zinc addition in up to 64% ee: Rosini, C.; Franzini, L.; Iuliano, A.; Fini, D.; Salvadori, P. Tetrahedron: Asymmetry 1991, 2, 363. Reviews: (a) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. (c) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
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Complete experimental details can be found in the Supporting Information.
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