메뉴 건너뛰기




Volumn 8, Issue 21, 2006, Pages 4743-4746

Axially chiral directly β,β-linked bisporphyrins: Synthesis and stereostructure

Author keywords

[No Author keywords available]

Indexed keywords


EID: 33750312663     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061812o     Document Type: Article
Times cited : (61)

References (42)
  • 18
    • 8444248938 scopus 로고    scopus 로고
    • For a directly β,β-linked, yet N-confused, porphyrin dimer that might be axially chiral but has not been stereochemically characterized, see: Chmielewski, P. J. Angew. Chem., Int. Ed. 2004, 43, 5655.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 5655
    • Chmielewski, P.J.1
  • 21
    • 33747475119 scopus 로고    scopus 로고
    • 2 in DMF as the solvent, the ring-annulated product was obtained in up to 95% yield. During the reviewing process, a similar cyclization reaction was reported, however, with lower yields: Shen, D.-M.; Liu, C.; Chen, Q.-Y. J. Org. Chem. 2006, 71, 6508.
    • (2006) J. Org. Chem. , vol.71 , pp. 6508
    • Shen, D.-M.1    Liu, C.2    Chen, Q.-Y.3
  • 24
    • 33750340828 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of TPP is available in the Supporting Information.
  • 27
    • 33750304993 scopus 로고    scopus 로고
    • note
    • 12
  • 28
    • 33750350123 scopus 로고    scopus 로고
    • note
    • Further chromatographic details: using a Chiralcel OD-H column (Daicel), 7°C, a flow rate of 0.3 mL/min, and n-hexane/2-propanol = 60: 40 as the eluent, or even more efficiently in the case of 4b, using a Chirex 3010 column (Phenomenex), 25°C, a flow rate of 1 mL/min, and n-hexane/ dichloromethane = 60:40 as the eluent.
  • 29
    • 33750310360 scopus 로고    scopus 로고
    • note
    • This chromatographic order is true for both chiral adsorbants used, Chiralcel OD-H (Daicel) and Chirex 3010 (Phenomenex).
  • 30
    • 0000750794 scopus 로고    scopus 로고
    • Schreier, P., Herderich, M., Humpf, H. U., Schwab, W., Eds.; Vieweg: Wiesbaden
    • Bringmann, G.; Busemann, S. Natural Product Analysis; Schreier, P., Herderich, M., Humpf, H. U., Schwab, W., Eds.; Vieweg: Wiesbaden, 1998; p 195.
    • (1998) Natural Product Analysis , pp. 195
    • Bringmann, G.1    Busemann, S.2
  • 33
    • 33750308355 scopus 로고    scopus 로고
    • note
    • Because Zn is not parametrized in the program packages that were used for the semiempirical calculation of excited states, the metal-free analogue of 4a was investigated instead. This approximation seemed justified because the presence or absence of Zn should not influence the shape of the CD curve substantially.
  • 35
    • 33750318566 scopus 로고    scopus 로고
    • note
    • To verify this assumption, three additional PM3 minimum geometries were also optimized with B3LYP/3-21G providing CD spectra identical to the one of the global minimum.
  • 39
    • 33750316648 scopus 로고    scopus 로고
    • note
    • 2-symmetry, the same applies for the phenyl group at C-5′ (which, in turn, is bent away from the porphyrin substituent at C-3′).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.