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Volumn 9, Issue 2, 2007, Pages 223-226

Enantiopure pseudo-C3-symmetric titanium alkoxide with propeller-like chirality

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; ORGANOMETALLIC COMPOUND; TITANIUM;

EID: 33846571402     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062655w     Document Type: Article
Times cited : (47)

References (26)
  • 17
    • 0000306923 scopus 로고    scopus 로고
    • 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
    • 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.
  • 20
    • 33846606096 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 21
    • 2142827189 scopus 로고    scopus 로고
    • 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
    • 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)
  • 22
    • 33644773399 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 24
    • 33846571960 scopus 로고    scopus 로고
    • 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
    • -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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.