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Volumn 17, Issue 10, 1998, Pages 1984-1992

A new set of structurally related enantiopure polypyrazolyl ligands of varying rotational symmetry: Synthesis, metal complexation, and comparison of asymmetric induction

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Indexed keywords


EID: 0000766087     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9801047     Document Type: Article
Times cited : (50)

References (64)
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    • Selected references: (a) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339-345. (b) Pfaltz, A. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag: Berlin, 1989; Vol. 5, pp 198-248. (c) Doyle, M. P. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 63-99. (d) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728. (e) Park, S.-B.; Murata, K.; Matsumoto, K.; Nishiyama, H. Tetrahedron 1995, 6, 2487-2494. (f) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247-1262.
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    • note
    • 2 was not evolved, even when the temperature was raised to 340 °C for 6 h. An intractable mixture resulted from this procedure. This strange behavior remains unexplained, but it implies that the cis/trans isomerization process which occurs during the Tp synthesis is somehow linked to Tp formation (or occurs afterwards).
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    • 2, which was found in a preliminary X-ray crystal structure (marred by disorder problems) to be analogous to several other published dimers of achiral Tp and bis(pyrazolyl)dihydroborate ligands that have two-coordinate Cu(I) ions in a linear geometry bridged by two bidentate chelates. See ref 12 and (a) Carrier, S. M.; Ruggiero, C. E.; Houser, R. P.; Tolman, W. B. Inorg. Chem. 1993, 32, 4889-4899. (b) Houser, R. P. Ph.D. Thesis, University of Minnesota, Minneapolis, MN, 1996. (c) Yoon, K.; Parkin, G. Polyhedron 1995, 14, 811-821. (d) Kiani, S.; Long, J. R.; Stavropoulos, P. Inorg. Chim. Acta 1997, 263, 357-366.
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    • Ph.D. Thesis, University of Minnesota, Minneapolis, MN
    • 2, which was found in a preliminary X-ray crystal structure (marred by disorder problems) to be analogous to several other published dimers of achiral Tp and bis(pyrazolyl)dihydroborate ligands that have two-coordinate Cu(I) ions in a linear geometry bridged by two bidentate chelates. See ref 12 and (a) Carrier, S. M.; Ruggiero, C. E.; Houser, R. P.; Tolman, W. B. Inorg. Chem. 1993, 32, 4889-4899. (b) Houser, R. P. Ph.D. Thesis, University of Minnesota, Minneapolis, MN, 1996. (c) Yoon, K.; Parkin, G. Polyhedron 1995, 14, 811-821. (d) Kiani, S.; Long, J. R.; Stavropoulos, P. Inorg. Chim. Acta 1997, 263, 357-366.
    • (1996)
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    • 2, which was found in a preliminary X-ray crystal structure (marred by disorder problems) to be analogous to several other published dimers of achiral Tp and bis(pyrazolyl)dihydroborate ligands that have two-coordinate Cu(I) ions in a linear geometry bridged by two bidentate chelates. See ref 12 and (a) Carrier, S. M.; Ruggiero, C. E.; Houser, R. P.; Tolman, W. B. Inorg. Chem. 1993, 32, 4889-4899. (b) Houser, R. P. Ph.D. Thesis, University of Minnesota, Minneapolis, MN, 1996. (c) Yoon, K.; Parkin, G. Polyhedron 1995, 14, 811-821. (d) Kiani, S.; Long, J. R.; Stavropoulos, P. Inorg. Chim. Acta 1997, 263, 357-366.
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    • 2, which was found in a preliminary X-ray crystal structure (marred by disorder problems) to be analogous to several other published dimers of achiral Tp and bis(pyrazolyl)dihydroborate ligands that have two-coordinate Cu(I) ions in a linear geometry bridged by two bidentate chelates. See ref 12 and (a) Carrier, S. M.; Ruggiero, C. E.; Houser, R. P.; Tolman, W. B. Inorg. Chem. 1993, 32, 4889-4899. (b) Houser, R. P. Ph.D. Thesis, University of Minnesota, Minneapolis, MN, 1996. (c) Yoon, K.; Parkin, G. Polyhedron 1995, 14, 811-821. (d) Kiani, S.; Long, J. R.; Stavropoulos, P. Inorg. Chim. Acta 1997, 263, 357-366.
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    • For example, see: (a) Kitajima, N.; Fujisawa, K.; Fujimoto, C.; Moro-oka, Y.; Hashimoto, S.; Kitagawa, T.; Toriumi, K.; Tatsumi, K.; Nakamura, A. J. Am. Chem. Soc. 1992, 114, 1277-1291. (b) Dias, R. H. V.; Kim, H.-J.; Lu, H.-L.; Rajeshwar, K.; de Tacconi, N. R.; Derecskei-Kovacs, A.; Marynick, D. S. Organometallics 1996, 15 ,2994-3003. (c) Ruggiero, C. E.; Carrier, S. M.; Antholine, W. E.; Whittaker, J. W.; Cramer, C. J.; Tolman, W. B. J. Am. Chem. Soc. 1993, 115, 11285-11298.
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    • For example, see: (a) Kitajima, N.; Fujisawa, K.; Fujimoto, C.; Moro-oka, Y.; Hashimoto, S.; Kitagawa, T.; Toriumi, K.; Tatsumi, K.; Nakamura, A. J. Am. Chem. Soc. 1992, 114, 1277-1291. (b) Dias, R. H. V.; Kim, H.-J.; Lu, H.-L.; Rajeshwar, K.; de Tacconi, N. R.; Derecskei-Kovacs, A.; Marynick, D. S. Organometallics 1996, 15 ,2994-3003. (c) Ruggiero, C. E.; Carrier, S. M.; Antholine, W. E.; Whittaker, J. W.; Cramer, C. J.; Tolman, W. B. J. Am. Chem. Soc. 1993, 115, 11285-11298.
    • (1996) Organometallics , vol.15 , pp. 2994-3003
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    • For example, see: (a) Kitajima, N.; Fujisawa, K.; Fujimoto, C.; Moro-oka, Y.; Hashimoto, S.; Kitagawa, T.; Toriumi, K.; Tatsumi, K.; Nakamura, A. J. Am. Chem. Soc. 1992, 114, 1277-1291. (b) Dias, R. H. V.; Kim, H.-J.; Lu, H.-L.; Rajeshwar, K.; de Tacconi, N. R.; Derecskei-Kovacs, A.; Marynick, D. S. Organometallics 1996, 15 ,2994-3003. (c) Ruggiero, C. E.; Carrier, S. M.; Antholine, W. E.; Whittaker, J. W.; Cramer, C. J.; Tolman, W. B. J. Am. Chem. Soc. 1993, 115, 11285-11298.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 11285-11298
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    • Unpublished results
    • + in which a pyrazolyl arm dangles free. (a) Kettler, P. B.; Tokar, C. J.; Tolman, W. B. Unpublished results. (b) Tokar, C. J.; Kettler, P. B.; Tolman, W. B. Organometallics 1992, 11, 2738-2739.
    • Kettler, P.B.1    Tokar, C.J.2    Tolman, W.B.3
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    • + in which a pyrazolyl arm dangles free. (a) Kettler, P. B.; Tokar, C. J.; Tolman, W. B. Unpublished results. (b) Tokar, C. J.; Kettler, P. B.; Tolman, W. B. Organometallics 1992, 11, 2738-2739.
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    • note
    • 3CN).
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    • Complete enantiocontrol at the metal was observed in intramolecular C-H bond activation reactions of rhodium complexes of 2 and 3, see: Keyes, M. C.; Young, V. G., Jr.; Tolman, W. B. Organometallics 1996, 15, 4133-4140.
    • (1996) Organometallics , vol.15 , pp. 4133-4140
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    • note
    • 3-aymmetric ligand disassociates during the reaction (ref 6b).
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    • Reference 31, p 534
    • Reference 31, p 534.
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    • SHELXTL-Plus V5.0, Siemens Industrial Automation, Inc.: Madison, WI.
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