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Volumn 15, Issue 24, 2004, Pages 3861-3867

Electronic effects on enantioselectivity in epoxidation catalyzed by D 4-symmetric chiral porphyrins

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; PORPHYRIN DERIVATIVE;

EID: 9944242226     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.10.029     Document Type: Article
Times cited : (17)

References (23)
  • 14
    • 9944227536 scopus 로고    scopus 로고
    • note
    • --migration (phenylacetaldehyde derivatives) was detected in each reaction (<2%)
  • 16
    • 9944237632 scopus 로고    scopus 로고
    • note
    • In Fig. 2, the plot of 4-substituted styrenes deviates from the linear correlation rather than that of 3-substituted styrenes. The deviation would be caused by the steric or electronic interaction between the substituents at the 4-position of styrenes and methoxymethyl moieties of the porphyrin
  • 18
    • 0028231555 scopus 로고
    • The major enantiomer of the cis-oxide had a (1S,2R)-configuration, which was derived from minor benzyl cation intermediate. The cis/trans ratio at the ring closure step should be different between the major pathway and the minor one, because the major and minor intermediates are diastereomers and therefore the lifetime and the steric circumstances between these intermediates would differ. There would be a tendency that the favored intermediate selectively affords the major diastereomer of the product, while the minor intermediate preferentially gives the minor diastereomer: W. Zhang, N.H. Lee, and E.N. Jacobsen J. Am. Chem. Soc. 116 1994 425
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 425
    • Zhang, W.1    Lee, N.H.2    Jacobsen, E.N.3
  • 19
    • 0034669482 scopus 로고    scopus 로고
    • In iron porphyrin-catalyzed oxidation with iodosylarenes, a Ph-IO-ligated complex of the catalyst is proposed to be a major active oxidant in the presence of olefins. For the mechanism of the oxidation by metalloporphyrin with PhIO, see: J.P. Collman, A.S. Chien, T.A. Eberspacher, and J.I. Brauman J. Am. Chem. Soc. 122 2000 11098
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 11098
    • Collman, J.P.1    Chien, A.S.2    Eberspacher, T.A.3    Brauman, J.I.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.