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Volumn 46, Issue 39, 2007, Pages 7432-7436

Synthesis, characterization, and chirality of dimeric N-confused porphyrin-zinc complexes: Toward the enantioselective synthesis of bis(porphyrinoid) systems

Author keywords

Chiral recognition; Chirality; Enantioselectivity; Porphyrinoids

Indexed keywords

CHIRALITY; COMPLEXATION; DICHROISM; ENANTIOMERS; ENANTIOSELECTIVITY; SYNTHESIS (CHEMICAL);

EID: 35048860410     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701860     Document Type: Article
Times cited : (40)

References (60)
  • 4
  • 8
  • 14
  • 18
  • 39
  • 41
    • 26844468968 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 6417.
    • (2005) Chem. Int. Ed , vol.44 , pp. 6417
    • Angew1
  • 43
    • 35048829199 scopus 로고    scopus 로고
    • 2O molecule, were observed for the crystals grown from a benzene/heptane mixture; see the Supporting Information for details.
    • 2O molecule, were observed for the crystals grown from a benzene/heptane mixture; see the Supporting Information for details.
  • 44
    • 35048883302 scopus 로고    scopus 로고
    • 2 differs from that of bivalves, in which the valves are hetoerochiral and the shell is effectively achiral.
    • 2 differs from that of bivalves, in which the valves are hetoerochiral and the shell is effectively achiral.
  • 45
    • 35048852442 scopus 로고    scopus 로고
    • 2-(1R,2S,5R)-menthol adducts comprising hydrogen-bonding systems analogous to that observed for the water molecule is inconclusive in regard to distinguishing the stability of the diastereomers; see the Supporting Information for details.
    • 2-(1R,2S,5R)-menthol adducts comprising hydrogen-bonding systems analogous to that observed for the water molecule is inconclusive in regard to distinguishing the stability of the diastereomers; see the Supporting Information for details.
  • 46
    • 35048882336 scopus 로고    scopus 로고
    • 1H NMR spectroscopy. The crude reaction mixture contained 3-tart and less than 10% of the demetalation product 2.
    • 1H NMR spectroscopy. The crude reaction mixture contained 3-tart and less than 10% of the demetalation product 2.
  • 57
  • 60
    • 35048877013 scopus 로고    scopus 로고
    • Although estimation of the enantiomeric excess is not feasible for this system, the ee value is probably lower for 4 than for its precursors, that is, 3-tart or 3-mal, as can be inferred on the basis of the considerably lower molar amplitudes of the CD signals. The simplified interpretation of the signs of the amplitude of the Cotton effect in the Soret region indicates an M configuration of the bis(2-aza-21- carbaporphyrinatosilver(III, units in 4 obtained from 3-(R,R)-tart (negative sign) and a P configuration for the assembly obtained by transmetalation of 3-(S,S)-tart and 3-(S)-mal (positive sign, 14] The shape of the CD couplets in the Soret region of 4 closely resembles those observed for chiral directly β,β- or meso,meso-linked bisporphyrinatozinc, 3,4] Since the orientation of the planar subunits in the X-ray structure of 4[8b
    • [3] are the same as those observed for 4 obtained from 3-(R,R)-tart for which we propose an M configuration on the basis of NMR data analysis


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.