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Dro, C.1
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0000306923
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In the most closely related example, Canary et al. employed a related chiral relay approach for controlling the helical symmetry of metal complexes derived from neutral tripodal tripyridyl ligands: Canary, J. W, Allen, C. S, Castagnetto, J. M, Wang, Y. J. Am. Chem. Soc. 1995, 117, 8484
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In the most closely related example, Canary et al. employed a related chiral relay approach for controlling the helical symmetry of metal complexes derived from neutral tripodal tripyridyl ligands: Canary, J. W.; Allen, C. S.; Castagnetto, J. M.; Wang, Y. J. Am. Chem. Soc. 1995, 117, 8484.
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For other, less closely related examples, see: a
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For other, less closely related examples, see: (a) Alajarín, M.; López-Leonardo, C.; Vidal, A.; Berná, J.; Steed, J. W. Angew. Chem., Int. Ed. 2002, 41, 1205.
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Alajarín, M.1
López-Leonardo, C.2
Vidal, A.3
Berná, J.4
Steed, J.W.5
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(b) Yao, Y.; Daley, C. J. A.; McDonald, R.; Bergens, S. H. Organometallics 1997, 16, 1890.
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Yao, Y.1
Daley, C.J.A.2
McDonald, R.3
Bergens, S.H.4
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33846606096
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The configuration of the newly formed stereocenter of amine (R,R)-8 was assigned as (R) from an established literature precedent for addition of methyllithium to this class of chiral imine and subsequently confirmed from analysis of the X-ray crystal structure of (R,M)-12. See: Bernardinelli, G.; Fernandez, D.; Gosmini, R.; Meier, P.; Ripa, A.; Schupfer, P.; Treptow, B.; Kundig, E. P. Chirality 2000, 12, 529.
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The configuration of the newly formed stereocenter of amine (R,R)-8 was assigned as (R) from an established literature precedent for addition of methyllithium to this class of chiral imine and subsequently confirmed from analysis of the X-ray crystal structure of (R,M)-12. See: Bernardinelli, G.; Fernandez, D.; Gosmini, R.; Meier, P.; Ripa, A.; Schupfer, P.; Treptow, B.; Kundig, E. P. Chirality 2000, 12, 529.
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2142827189
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A similarly poor yield was obtained for addition of methyllithium to the structurally related imine (R)-13 under these conditions. See: Kundig, E. P, Botuha, C, Lemercier, G, Romanens, P, Saudan, L, Thibault, S. Helv. Chim. Acta 2004, 87, 561, Chemical Equation Presented
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A similarly poor yield was obtained for addition of methyllithium to the structurally related imine (R)-13 under these conditions. See: Kundig, E. P.; Botuha, C.; Lemercier, G.; Romanens, P.; Saudan, L.; Thibault, S. Helv. Chim. Acta 2004, 87, 561. (Chemical Equation Presented)
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22
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33644773399
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The configuration and enantiomeric purity of amine (R)-9 was confirmed as >95% ee using our recently published NMR chiral derivatization protocol involving treatment with 2-formyl-phenylboronic acid and enantiopure BINOL. See: Pérez-Fuertes, Y.; Kelly, A. M.; Johnson, A. L.; Arimori, S.; Bull, S. D.; James, T. D. Org. Lett. 2006, 8, 609.
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The configuration and enantiomeric purity of amine (R)-9 was confirmed as >95% ee using our recently published NMR chiral derivatization protocol involving treatment with 2-formyl-phenylboronic acid and enantiopure BINOL. See: Pérez-Fuertes, Y.; Kelly, A. M.; Johnson, A. L.; Arimori, S.; Bull, S. D.; James, T. D. Org. Lett. 2006, 8, 609.
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Prins, L. J.; Blásquez, M.; Kolarovi, A.; Licini, G. Tetrahedron Lett. 2006, 47, 2735.
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(2006)
Tetrahedron Lett
, vol.47
, pp. 2735
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Prins, L.J.1
Blásquez, M.2
Kolarovi, A.3
Licini, G.4
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Crystal data: C55H89NO4Ti, M, 876.17, yellow prism, 0.40 x 0.30 x 0.25 mm3, tetragonal, space group P43, a, b, 14.584(2, c, 25.374(4) Å, V, 5396.87(13) Å3, Z, 4, Dc, 1.078 g/cm3, F000, 1920, Mo Ka radiation, λ, 0.71073 Å, T, 150(2) K, 2θmax, 55.0°, 21 199 reflections collected, 11 331 unique (Rint, 0.0279, Final GOF, 1.024, R1, 0.0560, wR2, 0.1464, R indices based on 9438 reflections with I > 2σ(I, refinement on F2, 573 parameters, 1 restraint, μ, 0.200 mm-1. Absolute structure parameter, 0.023, All non-hydrogen atoms were refined anisotropically. Hydrogen atoms were calculated at idealized positions and refined using the riding model. The largest peak and hole in th
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-3. Crystallographic data have been deposited at the Cambridge Crystallographic Data Centre with reference number CCDC 623640. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif.
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Bringmann, G.; Pfeifer, R. M.; Rummey, C.; Hartner, K.; Breuning, M. J. Org. Chem. 2003, 68, 6859.
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(2003)
J. Org. Chem
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, pp. 6859
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Bringmann, G.1
Pfeifer, R.M.2
Rummey, C.3
Hartner, K.4
Breuning, M.5
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