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Volumn 130, Issue 20, 2008, Pages 6507-6514

Synthesis, resolution, and VCD analysis of an enantiopure diazaoxatricornan derivative

Author keywords

[No Author keywords available]

Indexed keywords

CHIRALITY; DERIVATIVES; DICHROISM; PHASE STABILITY; SYNTHESIS (CHEMICAL);

EID: 43949088504     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja800262j     Document Type: Article
Times cited : (44)

References (66)
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    • (a) Aprahamian, I1; Eisenberg, D.; Hoffman, R. E.; Sternfeld, T.; Matsuo, Y.; Jackson, E. A.; Nakamura, E.; Scott, L. T.; Sheradsky, T.; Rabinovitz, M. J. Am. Chem. Soc. 2005, 127, 9581-9587.
  • 21
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    • In this study, we are only considering fully ring-closed polycyclic structures devoid of preexisting stereogenic centers or elements. For examples of such molecules, see: a
    • In this study, we are only considering fully ring-closed polycyclic structures devoid of preexisting stereogenic centers or elements. For examples of such molecules, see: (a) Na, J. E.; Lee, K. Y.; Seo, J.; Kim, J. N. Tetrahedron Lett. 2005, 46, 4505-4508.
    • (2005) Tetrahedron Lett , vol.46 , pp. 4505-4508
    • Na, J.E.1    Lee, K.Y.2    Seo, J.3    Kim, J.N.4
  • 22
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    • Compound 5 belongs to a whole family of novel stable carbenium ions: (a) Laursen, B. W.; Krebs, F. C.; Nielsen, M. F.; Bechgaard, K.; Christensen, J. B.; Harrit, N J. Am. Chem. Soc. 1998, 120, 12255-12263.
    • Compound 5 belongs to a whole family of novel stable carbenium ions: (a) Laursen, B. W.; Krebs, F. C.; Nielsen, M. F.; Bechgaard, K.; Christensen, J. B.; Harrit, N J. Am. Chem. Soc. 1998, 120, 12255-12263.
  • 41
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    • Cations 5 are, most probably, strong electrofugal groups: (a) Laleu, B.; Mobian, P.; Herse, C.; Laursen, B. W.; Hopfgartner, G.; Bernardinelli, G.; Lacour, J. Angew. Chem., Int. Ed. 2005, 44, 1879-1883.
    • Cations 5 are, most probably, strong electrofugal groups: (a) Laleu, B.; Mobian, P.; Herse, C.; Laursen, B. W.; Hopfgartner, G.; Bernardinelli, G.; Lacour, J. Angew. Chem., Int. Ed. 2005, 44, 1879-1883.
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    • Only symmetrical diazaoxatriangulenium derivatives with the same substituents on the nitrogen atoms have been reported so far
    • Only symmetrical diazaoxatriangulenium derivatives with the same substituents on the nitrogen atoms have been reported so far.
  • 46
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    • 4]. For examples, see: (a) Shinkai, S.; Hamada, H.; Kuroda, H.; Manabe, O. J. Org. Chem. 1981, 46, 2333-2338.
    • 4]. For examples, see: (a) Shinkai, S.; Hamada, H.; Kuroda, H.; Manabe, O. J. Org. Chem. 1981, 46, 2333-2338.
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    • The unusual peak shape and elution profile on Chiralcel OJ (Figure 4, top trace) of the enantiomers of 6a is a known phenomenon in enantioselective chromatography and has been observed in some instances in our laboratories and other research groups. Although we have no clear explanation for this feature, it indicates that both enantiomers exhibit quite different adsorption kinetics, suggesting that they interact with different sites within the chiral polymer matrix.
    • The unusual peak shape and elution profile on Chiralcel OJ (Figure 4, top trace) of the enantiomers of 6a is a known phenomenon in enantioselective chromatography and has been observed in some instances in our laboratories and other research groups. Although we have no clear explanation for this feature, it indicates that both enantiomers exhibit quite different adsorption kinetics, suggesting that they interact with different sites within the chiral polymer matrix.
  • 59
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    • 3 center has been performed according to the sequence rules detailed in the following articles: (a) Cahn, R. S.; Ingold, C.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1966, 5, 385-415.
    • 3 center has been performed according to the sequence rules detailed in the following articles: (a) Cahn, R. S.; Ingold, C.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1966, 5, 385-415.
  • 60
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    • 2 carbon closer to the O atom and the NPh moiety, respectively, then (ii) the carbon between the O atom and the NPr group, and finally (iii) the carbon flanked by the NPh and NPr moities, with the apical methyl group being the substituent with the lowest priority of all.
    • 2 carbon closer to the O atom and the NPh moiety, respectively, then (ii) the carbon between the O atom and the NPr group, and finally (iii) the carbon flanked by the NPh and NPr moities, with the apical methyl group being the substituent with the lowest priority of all.
  • 61
    • 43949121492 scopus 로고    scopus 로고
    • IR and VCD spectra for all nine conformers of (S)-6a are reported in the Supporting Information.
    • IR and VCD spectra for all nine conformers of (S)-6a are reported in the Supporting Information.
  • 62
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    • Even if the agreement between calculated and experimental IR and VCD spectra is not perfect, absolute configuration can be still determined. Indeed, some characteristic bands such as modes 16,17, 21, 3, and 6 can be assigned without ambiguity.
    • Even if the agreement between calculated and experimental IR and VCD spectra is not perfect, absolute configuration can be still determined. Indeed, some characteristic bands such as modes 16,17, 21, 3, and 6 can be assigned without ambiguity.
  • 63
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.